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-89ebe9ab13114b9386ea938495574c28

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268835B2