Category: 19472-74-3

Reference of 19472-74-3, These common heterocyclic compound, 19472-74-3, name is 2-Bromophenylacetonitrile, its 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.

Anhydrous ethanol (300 ml) was added to the eggplant-shaped flask at room temperature, stirred, and sodium metal (1.38 g, 60 mmol) was added under a nitrogen atmosphere until sodium was completely dissolved to obtain sodium ethoxide. The compound of the formula (1A) (34.1 g, 200 mmol) was added to a fresh solution of sodium ethoxide in ethanol. The compound represented by the formula (2) (49.4 g, 252 mmol) was added under stirring. The reaction was carried out at 35 C for 3-5 h until the reaction was completed. After cooling and suction filtration, the cake was washed with ethanol (10 ml) and dried to give a white solid (59.3 g, yield: 85%).

Statistics shows that 2-Bromophenylacetonitrile is playing an increasingly important role. we look forward to future research findings about 19472-74-3.

Reference:
Patent; Yangpu Huigu Pharmaceutical Co., Ltd.; Guo De; (24 pag.)CN104974167; (2019); B;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 19472-74-3, name is 2-Bromophenylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H6BrN

General procedure: Step 1: To an 8-mL culture tube with stir bar was added lithium chloride (1.1 equiv) and the flask was flame-dried under vacuum and cooled under an atmosphere of N2. THF (1.0 M) was added, followed by the appropriate nitrile (1.0 equiv). While stirring, methylmagnesium bromide (1.1 equiv of a solution in Et2O) was added dropwise at r.t., and the solutionwas stirred at r.t. for 30 min under an atmosphere of N2. A 1.1M stock solution of dimethylmanononitrile (DMMN) or dibenzylmalononitrile (DBMN) inTHF was prepared and added at r.t. (1.1 equiv of a 1.1M solution inTHF, reaction volume 0.50M with respect to nitrile starting material). The reaction was stirred at 80 C for 6 h under an atmosphere of N2. Step 2: The reaction was cooled to r.t. and DMF was added to bring the reaction solvent to a 1:1 THF/DMF ratio (0.25Mof a 1:1 THF/DMF mixture with respect to nitrile starting material). The desired electrophile (1.2 equiv) was added in a single portion. Ifthe electrophile was a solid, it was added with the DMF as a 0.60Mstock solution. The reaction was stirred at 80 C for 16 h, or until complete conversion was achieved as judged by TLC. The reaction was cooled to r.t., opened to air, quenched with 1M aq. HCl, and extracted with EtOAc (3). The organic fractions were combined,dried over MgSO4, and concentrated. The crude residue was purified by flash column chromatography to yield the desired malononitrile.

The synthetic route of 19472-74-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mills, L. Reginald; Rousseaux, Sophie A.L.; Tetrahedron; vol. 75; 32; (2019); p. 4298 – 4306;,
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Application of 19472-74-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 19472-74-3, name is 2-Bromophenylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(2-Methylpyridin-3-yl)boronic acid (550 mg, 3.2 mmol), 2-(2-bromophenyl)acetonitrile (597 mg, 3.05 mmol), Pd(PPh3)4 (176 mg, 0.15 mmol) and K2C03 (176 mg, 0.15 mmol) were dissolved in /’PrOH (5 mL) and water (2 mL) and the mixture was heated at 80 C under N2 for 5h. The mixture was filtered and the solid was washed with DCM (20 mL). The filtrate was washed with brine, dried over sodium sulfate and concentrated. Column chromatography (DCM/MeOH = 100:0 – 20:1) gave the product (300 mg, 45% yield) as a yellow solid. LCMS (ES-API): Rt 0.44 min; m/z 209.1 [M+H]+.

The synthetic route of 2-Bromophenylacetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CTXT PTY LIMITED; MORROW, Benjamin Joseph; FOITZIK, Richard Charles; CAMERINO, Michelle Ang; LAGIAKOS, Helen Rachel; WALKER, Scott Raymond; BOZIKIS, Ylva Elisabet Bergman; STEVENSON, Graeme Irvine; CUZZUPE, Anthony Nicholas; STUPPLE, Paul Anthony; (313 pag.)WO2019/43139; (2019); A1;,
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Application of 19472-74-3, These common heterocyclic compound, 19472-74-3, name is 2-Bromophenylacetonitrile, its 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.

General procedure: A flask was equipped with a magnetic stir bar and charged with 1Hpyrrole-2-carbaldehyde (2a; 19.0 mg, 0.2 mmol, 1.0 equiv), 2-bromophenylacetonitrile(1a; 39.2 mg, 0.2 mmol, 1.0 equiv), and K3PO4(63.6 mg, 0.3 mmol, 1.5 equiv). The flask was evacuated and filledwith N2, and then anhydrous DMSO (2.0 mL) was introduced via a syringe.The flask was heated in a 130 C oil bath for 24 h, at which timeTLC analysis [petroleum ether (bp 60-90 C)-EtOAc, 10:1] indicatedcomplete consumption of 2a and 1a. The reaction mixture was cooledto r.t. and added to a sat. solution of NaCl (20 mL) and extracted withEtOAc (3 ¡Á 10 mL). The combined organic layers were dried (Na2SO4)and filtered. The filtrate was concentrated, and the residue was purified by column chromatography on SiO2 [petroleum ether (bp 60-90C)-EtOAc, 10:1 to 30:1] to give 3ad; Yield: 40.5 mg (84%); fluorescent yellow solid; mp 193.7-194.6 C.

Statistics shows that 2-Bromophenylacetonitrile is playing an increasingly important role. we look forward to future research findings about 19472-74-3.

Reference:
Article; Jiang, Zeng-Qiang; Miao, Da-Zhuang; Tong, Yao; Pan, Qiang; Li, Xiao-Tong; Hu, Ren-He; Han, Shi-Qing; Synthesis; vol. 47; 13; (2015); p. 1913 – 1921;,
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19472-74-3, A common heterocyclic compound, 19472-74-3, name is 2-Bromophenylacetonitrile, molecular formula is C8H6BrN, its 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.

Example 33A A round bottom flask was charged under inert atmosphere with copper iodide (760 mg, 4 mmol), cesium carbonate (3.91 g, 12 mmol) then dimethylformamide (20 mL), previously degassed, was added followed by 2-Bromophenylacetonitrile (519 muL, 4 mmol), 3-Methylpyrazole (3.32 mL, 40 mmol) and N-N’-dimethylethylenediamine (425.86 muL, 4 mmol). The reaction mixture was heated to 120 C. for 2.5 hours. After cooling the reaction mixture was filtered through a Celite pad that was rinsed with dimethylformamide. The volume was reduced under reduced pressure, saturated ammonium chloride aqueous solution was added and extracted with ethyl acetate. The organic phase was washed with saturated aqueous NH4Cl solution, brine then dried over Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography on SiO2 using cyclohexane/ethyl acetate mixture of increasing polarity (from 100% cyclohexane to 100% ethyl acetate) as eluant. The oil obtained was further purified by SPE cartridge Stratosphere ?PL-THIOL MP? to remove copper salts. 300 mg of the title compound (38%) were obtained.GC-MS (Method 3A.1): Rt: 10.47 minMS: 197 [M]+.

The synthetic route of 19472-74-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/115863; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 19472-74-3, name is 2-Bromophenylacetonitrile, 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 19472-74-3, 19472-74-3

A/ Preparation of 2-(2′-bromophenyl)-2-methylpropionitrile: A solution of 2-(2′-bromophenyl)-acetonitrile (7.5 g; 38 mmole) and iodomethane (16.2 g; 114 mmole) in THF (30 ml) was slowly added (60 minutes) to a suspension of NaH (4.0 g; 100 mmole) in THF (100 ml) which had been refluxed in an inert atmosphere. The reaction was exothermic. Refluxing was continued for 2.5 h. The reaction mixture was then stirred at room temperature for 15 h. The solvent was evaporated off under reduced pressure; the residue was taken up in 100 ml of water and extracted with 2*100 ml of tertiobutylmethylether. The organic phases were combined, washed with 3*100 ml of a saturated NaCl solution; dried over MgSO4 then filtered. The solvent was evaporated off under reduced pressure. The desired product was obtained as a colorless oil after distillation under reduced pressure (T=125-140 C.; p=0.1 mbar). Yield=79%. This substance was also made using the procedure described by W. E. Parham and L. D. Jones (see J. Org. Chem., (1976), 41, pp 1187-1191) with a yield of 90%. Physical characteristics: 1 H NMR (CDCl3) 1.90 ppm (s; 6H); 7.19 ppm (m; 1H; J=7.5 Hz); 7.35 ppm (t; 1H; J=7.5 Hz); 7.49 ppm (m; 1H; J=7.5 Hz); 7.67 ppm (d; 1H; J=7.5 Hz). 13 C NMR: (CDCl3) 27.13 ppm; 37.64 ppm; 123.08 ppm; 123.92 ppm; 127.76 ppm; 128.49 ppm; 130.15 ppm; 136.18 ppm; 138.77 ppm. MS (IE; 70 eV) 225/223 (M+; 80%); 210/208 (100%); 183/181 (75%); 102 (20%).

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, 2-Bromophenylacetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Oxis Isle of Man, Limited; US5968920; (1999); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 19472-74-3, name is 2-Bromophenylacetonitrile, molecular formula is C8H6BrN, 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. 19472-74-3

The appropriate amount of organic solvent (volume ratio of 1: 1,4-dioxane and a mixture of DMSO (dimethyl sulfoxide). 2), the compound on 100mmol formula (I), 200mmol formula (II) compound, 8mmol bicomponent catalyst (as 4mmol (a-taPhos)2PdCl2And 4 mmolCu (TFA)2The mixture), 5mmol phosphine ligand L1 and methanesulfonic acid 20mmol acidic compound; and then stirred warmed to 60 , and the reaction was stirred at this temperature for 12 hours.After completion of the reaction, filtered hot and the filtrate was cooled to room temperature, and the pH was adjusted to neutral, and then washed with deionized water sufficiently shaken, and then ethyl acetate was added and extracted 3 times, the combined organic phase was concentrated under reduced pressure, the concentrate was subjected to silica gel column chromatography, a volume ratio of 1: 2 acetone – chloroform mixture to wash, to afford the compound of formula (III), in a yield of 97.3%.

The chemical industry reduces the impact on the environment during synthesis 2-Bromophenylacetonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Zhang, Yan; (9 pag.)CN105384674; (2016); A;,
Nitrile – Wikipedia,
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