Ethyl Bromide → HCID 11435291, compound

To a suspension of 0.42 g (10.5 mmol) NaH (60% dispersion in mineral oil) were added at ambient temperature 1.67 g (11 mmol) 4-chlorophenyl-acetonitrile in 10 ml anhydrous tetrahydrofuran. The reaction mixture was stirred at ambient temperature for 2 hours and then cooled to −20° C. 0.78 ml (10.5 mmol) Bromoethane was added drop-wise to the reaction mixture over 30 minutes. The reaction was warmed to ambient temperature while stirring over 2 hours. The reaction mixture was quenched by addition of 20 ml of saturated ammonium chloride solution. Dichloromethane was added, the organic phase was separated and the aqueous phase washed with dichloromethane. The combined organic phase was dried over MgSO4 and evaporated to afford rac-2-(4-chloro-phenyl)butyronitrile as a brown oil that did not require further purification. NMR (CDCl3, ppm): 0.80 (3H, t), 1.82 (2H, dq), 3.64 (1H, t), 7.30-7.15 (4H, m).

1. temperaturecooled to −20° C
2. temperatureThe reaction was warmed to ambient temperature
3. stirringwhile stirring over 2 hours
4. customThe reaction mixture was quenched by addition of 20 ml of saturated ammonium chloride solution
5. additionDichloromethane was added
6. customthe organic phase was separated
7. washthe aqueous phase washed with dichloromethane
8. dry with materialThe combined organic phase was dried over MgSO4
9. customevaporated

ORD record

ord-eea3466d3fef467998d16cddddbae2d5

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07875645B2