Sodium Cyanide → (4-Bromo-3-chlorophenyl)acetonitrile

Sodium cyanide (10.91 g, 222.52 mmol) in water (10 mL) was added to a solution of chloroform (20 mL) of N-benzyl-N,N-diethylethanaminium chloride (25.3 g, 111.26 mmol). 1-Bromo-4-(bromomethyl)-2-chlorobenzene (31.64 g, 111.26 mmol) in chloroform (5 mL) was added dropwisely at room temperature. The mixture was stirred at room temperature for 1 h then heated to 45° C. for additional 2 h. The reaction mixture was cooled, separated into two layers and the organic layer was washed with 0.5 N NaOH then brine. The chloroform layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash Silica chromatography {CombiFlash Companion—Presearch Ltd}, column size=330 g, flow rate=100 mL/min, elution gradient 0 to 100% EtOAc in isohexane over 40 minutes. Pure fractions were evaporated to dryness to afford 2-(4-bromo-3-chlorophenyl)acetonitrile (2.430 g, 9.48%) as a orange/yellow oil which solidified on standing.

1. temperaturethen heated to 45° C. for additional 2 h
2. temperatureThe reaction mixture was cooled
3. customseparated into two layers
4. washthe organic layer was washed with 0.5 N NaOH
5. dry with materialThe chloroform layer was dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude product was purified by flash Silica chromatography {CombiFlash Companion—Presearch Ltd}, column size=330 g, flow rate=100 mL/min, elution gradient 0 to 100% EtOAc in isohexane over 40 minutes
9. customPure fractions were evaporated to dryness

ORD record

ord-5b50dda1179c4f23881d7152401227cc

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188092B2