Water → 2-(4-Fluoro-2-methylphenyl)acetonitrile

1-(Chloromethyl)-4-fluoro-2-methylbenzene (12.8 g, 81 mmol) was dissolved in CH2Cl2 (50 mL) and to the resultant solution was added a mixture of tetrabutylammonium hydrogensulphate (1.4 g, 4.0 mmol), NaOH (0.32 g, 8.1 mmol) and water (50 mL) followed by an aqueous solution of potassium cyanide (5.0 g, 77 mmol). The mixture was stirred for 5 minutes and then the pH of the aqueous layer was monitored and adjusted to the alkaline side by the dropwise addition of aqueous sodium hydroxide (5M). The mixture was refluxed for one hour, stirred at room temperature overnight and then diluted with CH2Cl2 (50 mL). The organic layer was washed thrice with water and then dried over Na2SO4. The solvent was removed by evaporation and the product was purified by chromatography on silica gel using CH2Cl2. There was obtained 11.1 g (92%) of (4-fluoro-2-methylphenyl)acetonitrile as an oil. 1H NMR (300 MHz, CDCl3): 2.3 (s, 3H), 3.6 (s, 2H), 6.8-7.0 (m, 2H), 7.3 (m, 1H).

1. additionwas added
2. temperatureThe mixture was refluxed for one hour
3. stirringstirred at room temperature overnight
4. washThe organic layer was washed thrice with water
5. dry with materialdried over Na2SO4
6. customThe solvent was removed by evaporation
7. customthe product was purified by chromatography on silica gel

ORD record

ord-01054615c17941d483e326a57166d9c7

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402581B2