Category: 170572-49-3

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H6FN

1,2-Dichloroethane (151 kg) was charged to a suitable vessel along with 4-cyano-2-fluorotoluene (24 kg) and AIBN (2 kg). The mixture was heated to 7074 C. Once the batch temperature reached 70 C., N-bromosuccinimide (47.4 kg) was added in portions at the rate of 12 kg/h, maintaining the temperature at 7074 C. (it is important to control addition rate to avoid exothermic reaction). The mixture was sampled via GC detection after 24 kg of N-bromosuccinimide was added, and the reaction was heated at 70-74 C. until complete reaction was observed. The mixture was cooled to 0-5 C. and allowed to stand for 2 additional hours. The mixture was filtered, and the cake was washed with MTBE (24 kg). The filtrate was washed with water (3×65 kg). The organic layer was dried with sodium sulfate (10.3 kg) for 6 hours, filtered and the cake was washed with MTBE (24 kg). The solution was evaporated under reduced pressure, ethanol (12 kg) was added and the mixture was heated to 40-45 C., then cooled slowly to 0-5 C. while stirring to crystallize. The mixture was filtered and the cake was washed with cold ethanol (5 kg). The crude solid was recrystallized from petroleum ether, filtered and washed with petroleum ether (10 kg), giving the title compound 4-(bromomethyl)-3-fluorobenzonitrile as an off white solid (21 kg, 55% yield). 1H NMR (300 MHz, CDCl3) delta ppm 4.46-4.50 (m, 2H) 7.36 (dd, J=8.85, 1.32 Hz, 1H) 7.44 (dd, J=7.91, 1.32 Hz, 1H) 7.52 (dd, J=7.91, 7.16 Hz, 1H). 13C NMR (75 MHz, CDCl3) 8 ppm 23.65 (d, J=4.60 Hz, 1C) 113.76 (d, J=9.77 Hz, 1C) 117.09 (d, J=2.87 Hz, 1C) 119.44 (d, J=24.71 Hz, 1C) 128.44 (d, J=4.02 Hz, 1C) 130.66-130.81 (s, 1C) 130.81-131.06 (s, 1C) 132.18 (d, J=3.45 Hz, 1C) 159.86 (d, J=254.03 Hz, 1C). IR: (KBr) 3088, 3077, 3040, 2982, 2250, 1571, 1508, 1439, 1248 cm-1.Anal. Calcd for C8H5BrFN: Calc. C, 44.89; H, 2.35; N, 6.54; F, 8.88. Found: C, 44.94; H, 2.73; N, 6.56; F, 8.73.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 170572-49-3.

Reference:
Patent; Bristol-Myers Squibb Company; US2010/240719; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H6FN

To a heterogenous solution of 3-fluoro-4-methyl-benzonitrile (5 g, 37.0 mmol) in ethanol (125 mL) at 25C was added hydroxylamine hydrochloride (5.14 g, 74 mmol) and triethylamine (10.3 mL, 74 mmol). The reaction mixture was heated at 80C for 1 hour. After cooling to room temperature volatiles were removed under reduced pressure thus affording a white gum that was used in the next step without any purification. LC/MS (Method A) retention time = 0.25 minutes, 169.3 (M+H). (0416) NMR (400 MHz, DMSO-de) delta ppm: 7.44 (t, 2H), 7.32 (d, 1 H), 5.85 (brs, 2H), 4.50 (brs, 1 H) 2.24 (s, 3H). (0417) 9F NMR (400 MHz, DMSO-de) delta ppm: -1 14.46 (s).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 170572-49-3.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; HOFFMAN, Thomas, James; STIERLI, Daniel; BEAUDEGNIES, Renaud; POULIOT, Martin; HAAS, Ulrich, Johannes; (111 pag.)WO2018/219773; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 170572-49-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-fluoro-4-methylbenzonitrile (29.54 g) and NBS (46.7 g) as a suspension in 1,2-dichloroethane (500 ml) was treated with benzoyl peroxide (4.24 g) in a flask mounted with a reflux condenser open to air. The flask was immersed in an oil bath at 75 C and light shun on it with a sunlamp. A more vigorous reflux was suddenly observed and the reaction became homogeneous. The reaction was let stir at this temperature for a total of 2 hours then let cool to room temperature. Hexanes (500 ml) was added and the precipitate filtered and discarded. The filtrate was concentrated under reduced pressure to approximately 100 ml and taken up in ethyl acetate (200 ml). The reaction was washed with half saturated sodium bicarbonate (100 ml), then brine (100 ml). The organic layer was separated and dried over magnesium sulfate. The organic phase was concentrated under reduced pressure to give the benzylic bromide as a yellow solid that was used as such in the next step.

The chemical industry reduces the impact on the environment during synthesis 3-Fluoro-4-methylbenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2009/67797; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 170572-49-3,Some common heterocyclic compound, 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, molecular formula is C8H6FN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Method B The reaction was carried out with the aid of a washer filled with sodium hypochlorite solution. 3-Fluoro-4-methylbenzonitrile (200 g, 1479.9 mmol) was initially charged in DMF (1.5 liters) and warmed to 40 C., and sodium methanethiolate (altogether 126.8 g, 1627.9 mmol) was added a little at a time (about 25 g per portion). During the addition, the temperature increased to 100 C. The reaction mixture was stirred initially at a bath temperature of 175 C. for 1.5 h and then at room temperature overnight. The reaction mixture was then poured into water (7.5 liters) and extracted twice with ethyl acetate (1875 ml each). The combined organic phases were washed with saturated sodium chloride solution (1875 ml) and concentrated on a rotary evaporator, and the residue was chromatographed on silica gel (mobile phase: petroleum ether/ethyl acetate 95:5, about 30 liters). Removal of the solvent on a rotary evaporator and drying under high vacuum gave 172 g (71% of theory) of the desired compound. GC-MS (Method 1): Rt=5.25 min; MS (ESIpos): m/z (%)=163.0 (100) [M]+ 1H-NMR (400 MHz, DMSO-d6): delta=2.30 (s, 3H), 2.54 (s, 3H), 7.38 (d, 1H), 7.52 (dd, 1H), 7.58 (br. s, 1H).

The synthetic route of 170572-49-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2011/34433; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 170572-49-3, Quality Control of 3-Fluoro-4-methylbenzonitrile

Example 11A 3-Fluoro-4-formylbenzonitrile The reaction was carried out under argon. 3-Fluoro-4-methylbenzonitrile (121 g, 895 mmol) and N,N-dimethylformamide dimethylacetal (245 g, 2.06 mol) were dissolved in DMF (1.8 liters) and stirred under reflux overnight. The content of the flask was then poured into water (2 liters), the mixture was extracted twice with ethyl acetate and the combined organic phases were washed with saturated sodium chloride solution. The organic phase was concentrated and the residue was redissolved in THF/water (1:1, 2.7 liters). Sodium periodate (503 g, 2.35 mol) was added, and the mixture was stirred at room temperature for one hour. The precipitate was then removed and the filtrate was recovered and extracted repeatedly with ethyl acetate. The combined organic phases were washed once with saturated sodium bicarbonate solution and once with saturated sodium chloride solution, dried and concentrated to give an oil. This oil was purified by column chromatography on silica gel (mobile phase: petroleum ether/dichloromethane 6:4, then 4:6, finally pure dichloromethane). The product fractions were concentrated. This gave 28.0 g (20% of theory) of the target compound as a white crystalline solid. GC-MS (Method 1): Rt=3.63 min; MS (ESIpos): m/z (%)=149.0 (48) [M]+, 150.0 (5) [M+H]+ 1H-NMR (400 MHz, DMSO-d6): delta=7.89 (d, 1H), 8.00 (t, 1H), 8.11 (d, 1H), 10.24 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Fluoro-4-methylbenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/94968; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

170572-49-3, A common compound: 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Intermediate 54 2- [4- (5-cyano-2-methylphenoxy)-2-methylphenoxy]-2-methylpropionic acid ethyl ester Step A . 3-fluoro-4-methyl-5-nitrobenzonitrile; Add potassium nitrate (4.51 g, 44.54 mmol) in three or four portions to 3-fluoro-4- methylbenzonitrile (6.02 g, 44.54 mmol) in concentrated H2SO4 (50 ml) at 0C and stir. Stir the deep orange solution for 2 hours at 0C and then for 1 hour at rt. Add the mixture over 800 ml of ice and extract with 150 ml of AcOEt. Allow the mixture to warm at rt and separate the organic layer. Extract again the aqueous layer with 100 ml of AcOEt. Combine the organic extracts and washed with water (50 ml) and brine (50 ml). Dry the organic layer over magnesium sulfate, filter, and concentrate under reduced pressure to give the crude product (7.64 g, 93% yield). Although the product can be used without further purification, flash chromatogapy can be performed in silica using hexane: ethyl acetate (10: 1) as eluent.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Fluoro-4-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/54176; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The chemical industry reduces the impact on the environment during synthesis 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, I believe this compound will play a more active role in future production and life. 170572-49-3

Preparation C; 4-(Bromomethyl)-3-fluorobenzonitrile; Method A. NBS/AIBN Bromination; 1,2-Dichloroethane (151 kg) was charged to a suitable vessel along with 4-cyano-2-fluorotoluene (24 kg) and AIBN (2 kg). The mixture was heated to 7074 C. Once the batch temperature reached 70 C., N-bromosuccinimide (47.4 kg) was added in portions at the rate of 12 kg/h, maintaining the temperature at 7074 C. (it is important to control addition rate to avoid exothermic reaction). The mixture was sampled via GC detection after 24 kg of N-bromosuccinimide was added, and the reaction was heated at 70-74 C. until complete reaction was observed. The mixture was cooled to 0-5 C. and allowed to stand for 2 additional hours. The mixture was filtered, and the cake was washed with MTBE (24 kg). The filtrate was washed with water (3¡Á65 kg). The organic layer was dried with sodium sulfate (10.3 kg) for 6 hours, filtered and the cake was washed with MTBE (24 kg). The solution was evaporated under reduced pressure, ethanol (12 kg) was added and the mixture was heated to 40-45 C., then cooled slowly to 0-5 C. while stirring to crystallize. The mixture was filtered and the cake was washed with cold ethanol (5 kg). The crude solid was recrystallized from petroleum ether, filtered and washed with petroleum ether (10 kg), giving the title compound 4-(bromomethyl)-3-fluorobenzonitrile as an off white solid (21 kg, 55% yield). 1H NMR (300 MHz, CDCl3) delta ppm 4.46-4.50 (m, 2 H) 7.36 (dd, J=8.85, 1.32 Hz, 1H) 7.44 (dd, J=7.91, 1.32 Hz, 1H) 7.52 (dd, J=7.91, 7.16 Hz, 1 H). 13C NMR (75 MHz, CDCl3) delta ppm 23.65 (d, J=4.60 Hz, 1C) 113.76 (d, J=9.77 Hz, 1C) 117.09 (d, J=2.87 Hz, 1C) 119.44 (d, J=24.71 Hz, 1C) 128.44 (d, J=4.02 Hz, 1C) 130.66-130.81 (s, 1C) 130.81-131.06 (s, 1C) 132.18 (d, J=3.45 Hz, 1C) 159.86 (d, J=254.03 Hz, 1C). IR: (KBr) 3088, 3077, 3040, 2982, 2250, 1571, 1508, 1439, 1248 cm-1.Anal. Calcd for C8H5BrFN: Calc.C,44.89; H, 2.35; N, 6.54; F, 8.88; Found: C, 44.94; H, 2.73; N, 6.56; F, 8.73.

The chemical industry reduces the impact on the environment during synthesis 170572-49-3. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/111858; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

170572-49-3, Adding a certain compound to certain chemical reactions, such as: 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 170572-49-3.

Method B. Sodium bromate Bromination To a suitable reactor was added dichloromethane (40 L) and 3-fluoro-4-methylbenzonitrile (4 kg, 18.7 mol) followed by a solution of sodium bromate in water (13.45 kg, 89.1 mol dissolved in 53.6 L water). The reaction mixture was cooled to 0-5 C. A solution of sodium bisulfite (9.25 kg dissolved in 42 L water) was added over a period of 2-3 hours while maintaining a batch temperature of 10-20 C. (the reaction is exothermic). After the addition was complete, a 200 W lamp was shined on the reactor and the batch temperature was increased to 25-30 C. The light and temperature were continued until product was 70-75% by HPLC. The light was removed, stirring was stopped and the reaction was permitted to settle for 15 minutes. The organic layer was removed and the remaining aqueous layer was extracted with dichloromethane twice. The organic layers were combined and washed four times with 10% sodium thiosulfate solution. The organic layer was then washed with brine (10 L) and dried with sodium sulfate. The organic layer was concentrated and then petroleum ether was added and distilled to dryness twice to remove all dichloromethane. Petroleum ether (3 L) was added and the slurry was cooled to 5-10 C. for 1 hour. The slurry was filtered and washed with cold petroleum ether. The product was dried in a vacuum oven at 40-45 C. to give the title compound (3.2 kg, 50.4% yield) as an off-white solid. Representative procedure for recovery of the title compound from mother liquor: The crude mass (~36% 4-(bromomethyl)-3-fluorobenzonitrile and 59% gem-dibromide) obtained from concentration of mother liquor (300 g) and 2 equivalents of diisopropyl ethyl amine (based on gem-dibromide) was dissolved in acetonitrile (3 L) and water (50 mL). The reaction was cooled to 0-5 C. and diethyl phosphite (169 g, 1.22 mol) was added over 30 minutes (addition was exothermic). The reaction was stirred for 60-90 min at 0-5 C. and was monitored by TLC. When dibromide was no longer present by TLC, water (3.3 L) was added and the resulting slurry was filtered. The filter cake was washed with water and dried in a vacuum oven (until the moisture content was <1%) to give 202 g (98 AP by HPLC) of additional title compound. According to the analysis of related databases, 170572-49-3, the application of this compound in the production field has become more and more popular. Reference:
Patent; Bristol-Myers Squibb Company; US2009/111858; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts