Water → 2-(4-Bromo-2-methylphenyl)acetonitrile

To a solution of 4-bromo-1-bromomethyl-2-methyl-benzene (3.96 g, 15 mmol) dissolved in DMF (16 mL) were added sodium cyanide (0.85 g, 17.25 mmol) and water (1.8 mL). The reaction was stirred for overnight at room temperature. To the reaction was added 100 mL water; 80 mL saturated NaHCO3, and 100 mL EtOAc. The layers were separated, and the aqueous layer was extracted with 3×100 mL EtOAc. The combined organics were washed with 100 mL water, and then dried over Na2SO4. After filtering off the solids, the mother liquor was concentrated to the desired product by rotary evaporation (2.92 g, 92.7% yield). 1H NMR (400 MHz, CDCl3): δ 2.32 (2H, s), 3.62 (1 H, s), 7.20-7.27 (1 H, m), 7.32-7.41 (1 H, m).

1. customThe layers were separated
2. extractionthe aqueous layer was extracted with 3×100 mL EtOAc
3. washThe combined organics were washed with 100 mL water
4. dry with materialdried over Na2SO4
5. filtrationAfter filtering off the solids
6. concentrationthe mother liquor was concentrated to the desired product by rotary evaporation (2.92 g, 92.7% yield)

ORD record

ord-e41ba1e8abbc431fb284ec6f582baeba

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268835B2