3,5-Dibromotoluene → 3-Bromo-5-methylbenzonitrile

Temperature

200 °C

To a solution of 3,5-dibromotoluene (10.00 g) in 1-methyl-2-pyrrolidone (70 ml) was added copper (I) cyanide (5.20) and the mixture was stirred at 200° C. for 1.5 hours. The reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The extract was washed with 1M hydrochloric acid, water and brine, dried over anhydrous magnesium sulfate and then concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=9/1 as an eluant to give the desired compound (1.70 g, yield 21%).

1. temperatureThe reaction mixture was cooled to room temperature
2. custompartitioned between water and ethyl acetate
3. washThe extract was washed with 1M hydrochloric acid, water and brine
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated in vacuo
6. customThe residue was purified by chromatography on a silica gel column

ORD record

ord-29464c95dfd64382810da458ad611d98

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06555556B1