Category: 75279-55-9

75279-55-9, name is 2-Chloro-6-fluorophenylacetonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of 2-Chloro-6-fluorophenylacetonitrile

N-(2,2-dimethyl-2-(2-chloro-6-fluoro)phenethyl)-N’-(2-thiazolyl)thiourea A solution of 2-chloro-6-fluorophenyl acetonitrile (1.69 g, 10 mmole) in dry THF (70 ml) was cooled to -60 C., and lithium diisopropylamide (5.25 ml, 10.5 mmole) was added. After 30 min, methyl iodide (0.68 ml, 11 ml) was added into the reaction mixture, and the reaction was slowly warmed to 0 C., and kept at 0 C. for 1 hr. Then it was cooled to -60 C. again, and more lithium diisopropylamide (6 ml, 12 mmole) was added. After 30 min, methyl iodide (1.87 ml, 30 mmole) was added. The reaction mixture was allowed to warm to room temperature and kept there for 2 hr after which it was poured into a sodium hydrogen carbonate solution, and extracted with chloroform. The organic phase was washed with water, dried, and the solvent was evaporated in vacuo. The product 2,2-dimethyl-2(2-chloro-6-fluorophenyl)acetonitrile (1.07 g) was isolated by silica gel column chromatography. 1 H-NMR (CDCl3) d: 7.25 (m, 2H, Ph), 7.03 (m, 1H, Ph), 1.98 (s, 3H, Me), 1.96 (s, 3H, Me).

The synthetic route of 75279-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Medivir AB; US5593993; (1997); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 75279-55-9, name is 2-Chloro-6-fluorophenylacetonitrile, 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 75279-55-9, HPLC of Formula: C8H5ClFN

General procedure: A mixture of 15.3 g (100 mmol) of 2-(2,6difluorophenyl)acetonitrile, 152.5 g (70 mL, 812 mmol) of dibromoethane, and 32.7 g (144 mmol) of Et3BnN+Cl- was isolated from moisture and carbon dioxide and vigorously stirred at 60. A solution prepared from 95 g (1430 mmol, ?84.5%) of KOH and 95 mL of water was then added dropwise; the mixture was stirred during 6 h at 60-65C, and left overnight. On the next day, the reaction mixture was extracted with t-BuOMe (3×100 mL), the combined organic fractions were evaporated, and residual water was removed via azeotropic distillation with toluene. Then 60 mL of water and 40 mL of concentrated sulfuric acid were added to the obtained 1-(2,6-difluorophenyl)cyclopropanecarbonitrile, and the mixture was refluxed during 4 h. The reaction mass was cooled to ambient; the precipitate was filtered off and dried. Yield 17.82 g (90%), mp 156-157 (toluene).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-6-fluorophenylacetonitrile, and friends who are interested can also refer to it.

Reference:
Article; Novakov; Yablokov; Navrotskii; Mkrtchyan; Vernigora; Babushkin; Kachala; Ruchko; Russian Journal of General Chemistry; vol. 87; 2; (2017); p. 224 – 230; Zh. Obshch. Khim.; vol. 87; 2; (2017); p. 247 – 254,8;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 75279-55-9, 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. 75279-55-9, name is 2-Chloro-6-fluorophenylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a cooed (0C) solution of suitable nitrile derivative (V) (1.0 eq) in EtOH (12.0 eq), acetyl chloride (8.0 eq) was added dropwise; the reaction flask was stoppered tightly and the reaction mixture was allowed to warm to r.t. and stirring was continued for 6 hrs at same temperature. Then the reaction was stopped, the solvent was removed under reduced pressure and the reaction mixture was cooled to 0C. Saturated NaHCO3 solution was added and the resulting mixture was stirred until gas evolution ceased. The product was extracted with Et2O and the organic solution was washed with H2O and brine. The organic layer was dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure; the crude product was purified by CC over silica gel, using EP/EtOAc 3:1 v/v as the eluent, to afford the pure desired intermediate 4. (y = 35%)

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-Chloro-6-fluorophenylacetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AXXAM S.p.A.; PEVARELLO, Paolo; SODANO, Mariangela; SEVERI, Elda; VITALONE, Rocco; THOMAS, Russell; (98 pag.)EP3398941; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 75279-55-9,Some common heterocyclic compound, 75279-55-9, name is 2-Chloro-6-fluorophenylacetonitrile, molecular formula is C8H5ClFN, 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: Typical procedure exemplified by the synthesis of 2-amino-4-chlorobenzo-1-thiophene-3-carbonitrile (Table 1, entry 5a): To a N2 flushed, 500 mL, three necked round bottomed flask were added 2-chloro-6-fluorophenylacetonitrile (1e) (8.48 g, 50 mmol) and DMSO (100 mL). To the solution was added 60% sodium hydride (2.10 g, 52.5 mmol) portion wise under N2 at rt (slightly exothermic). After 30 min, the reaction mixture was cooled to 15C with cold water bath and O-ethyl carbonisothiocyanatidate (2) (5.65 mL, 50.0 mmol) was added drop wise. After 1 h, the reaction mixture was heated at 100C for 2 h. A solution of 5 N NaOH (50 mL) was added and the reaction mixture was stirred at 100C for 2 h. The suspension was cooled to rt with stirring and 700 mL of water was added. The mixture was then cooled to 15C. The suspension was filtered and house vacuum air dried for 18 h to give the crude product as ayellow solid (6.5 g).

The synthetic route of 75279-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Krishnananthan, Subramaniam; Smith, Daniel; Traeger, Sarah C.; Mathur, Arvind; Li, Jianqing; Tetrahedron Letters; vol. 56; 24; (2015); p. 3766 – 3768;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 75279-55-9, A common heterocyclic compound, 75279-55-9, name is 2-Chloro-6-fluorophenylacetonitrile, molecular formula is C8H5ClFN, 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.

Similar results are obtained when the above reaction is repeated using substituted-phenylacetonitriles. For example, when 1,4-dichlorobutene-2 is reacted with 6-chloro-2-fluorophenylacetonitrile or 4-nitrophenylacetonitrile in accordance with the above process 1-cyano-1-(6-chloro-2-fluorophenyl)-2-vinylcyclopropane and 1-cyano-1-(4-nitrophenyl)-2-vinylcyclopropane are respectively produced.

The synthetic route of 75279-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; National Distillers and Chemical Corporation; US4399076; (1983); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 75279-55-9,Some common heterocyclic compound, 75279-55-9, name is 2-Chloro-6-fluorophenylacetonitrile, molecular formula is C8H5ClFN, 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.

Step 1–Preparation of alpha-[2-(4-chlorophenyl)ethyl]-2-chloro-6-fluorophenylacetonitrile A 3 neck 200 ml round bottom flask was charged with 7.5 gms of 60% NaH (0.187 mole, 1.5 eq.), washed three times with 25 ml hexanes, in 60 ml of 2:1 toluene:DMF. To this was added 21.2 gms (0.125 mole, 1.0 eq.) of 2-chloro-6-fluorophenylacetonitrile dropwise over 0.5 hour in 40 ml of 2:1 toluene:DMF. The reaction was stirred for 20 minutes at 10 C. then at room temperature for 1 hour after which 32.1 gms of 2-(4-chlorophenyl)ethyl methanesulfonate (0.137 mole, 1.1 eq.) in 60 ml of 2:1 toluene:DMF was added dropwise over 1 hour. Approximately 70 ml of 2:1 toluene:DMF was added to permit constant stirring and the reaction was stirred for an additional 3.5 hours after which gas liquid chromatography indicated the reaction was complete. Then 50 ml of water was added, followed by 10 ml of 10% HCl and 300 ml of ether. The ether was washed with 100 ml of water which was extracted twice with 50 ml of ether then washed with water. The combined ethers were dried and concentrated to give 40.0 gms of crude product which was distilled under reduced pressure. 26.6 gms (69.8%) of product resulted having a boiling point of 175-185 C. at 1 mm Hg. NMR (90 MHz): 2.2-2.9(m, 4H), 4.2-4.4(t, 1H) and 7.0-7.4(m, 7H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-6-fluorophenylacetonitrile, its application will become more common.

Reference:
Patent; Rohm and Haas Company; US5087635; (1992); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts