Potassium Cyanide → (4-Bromo-2-chlorophenyl)acetonitrile

To a magnetically stirring solution of 4-bromo-1-bromomethyl-2-chloro-benzene (3.59 g, 12.67 mmol) from step 2 above and tetrabutylammonium bromide (0.41 g, 1.27 mmol) in CH2Cl2/H2O 1:1 (60.0 mL), was added a solution of KCN (2.48 g, 38.01 mmol) in H2O (30 mL). The resulting orange mixture was stirred at room temperature for 3 hours. The layers of the resulting reaction mixture were separated and the organic layer was washed with NaHCO3 sat solution (3×50 mL), then dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (30% EtOAc in Hexanes) to yield the intermediate as a clear oil (3.59 g, 100%). 1H NMR (400 MHz, CDCl3): δ 3.79 (s, 2H), 7.37–7.60 (m, 3H).

1. customThe layers of the resulting reaction mixture
2. customwere separated
3. washthe organic layer was washed with NaHCO3
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe crude residue was purified by flash chromatography (30% EtOAc in Hexanes)

ORD record

ord-5cd1742f78a14744a4d9916cc6b3ecdf

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07151105B2