2-Bromopropane → HCID 13326401, compound

Temperature

45 °C

To a stirred solution of 50% sodium hydroxide (5.2 g, 65.2 mmol) there was added 4-fluorophenylacetonitrile (10.0 g, 74.1 mmol), sodium hydroxide pellets (0.7 g, 18.5 mmol) and tetrabutylammonium chloride (3.3 g, 14.1 mmol) and the reaction mixture was heated to 45° C. To the reaction mixture there was added 2-bromopropane (10.0 g, 81.5 mmol) and the reaction mixture heated at 60-65° C. for 1 hour, and then at 90-95° C. for 1 hour. The reaction mixture was cooled to ambient temperature. The reaction mixture was diluted with a mixture of 1:1 diethyl ether/water (100 mL). The layers were separated and the aqueous layer was washed with diethyl ether (25 mL). The organic layers were combined, washed with brine (25 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (silica gel, 30/70 methylene chloride/hexane) to give 9.4 g (71 % yield) of 4-fluoro-α-(1-methylethyl)benzeneacetonitrile as a white oil. 1H NMR (300 MHz, CDCl3) d 7.31 (m, 2H), 7.08 (m, 2H), 3.65 (d, 1H), 2.12 (m, 1H), 1.07 (d, 3H), 1.03 (d, 3H).

1. temperaturethe reaction mixture heated at 60-65° C. for 1 hour
2. temperatureThe reaction mixture was cooled to ambient temperature
3. customThe layers were separated
4. washthe aqueous layer was washed with diethyl ether (25 mL)
5. washwashed with brine (25 mL)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by flash chromatography (silica gel, 30/70 methylene chloride/hexane)

ORD record

ord-23cc5f30bc6b4e399c185786fe81736b

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06265439B1