Sodium Cyanide → 2-(4-Bromo-2-fluorophenyl)acetonitrile

Temperature

90 °C

To a stirred solution of 4-bromo-2-fluoro benzyl bromide (1.5 g, 5.6 mmol) in DMF (50 mL) was added sodium cyanide (0.8 g, 16.8 mmol). The resulting mixture was stirred at 90° C. for 1 h, cooled at rt and quenched with brine (50 mL). After extraction with EtOAc (3×50 mL), the organic layers were combined, washed with brine (50 mL), dried (MgSO4), and concentrated in vacuo. The residue was purified by chromatography on silica gel using a mixture of hexanes:EtOAc (5:1) to afford 4-bromo-2-fluoro benzyl cyanide as yellow solid. MS (ESI) 307 (M+H)+.

1. temperaturecooled at rt
2. customquenched with brine (50 mL)
3. extractionAfter extraction with EtOAc (3×50 mL)
4. washwashed with brine (50 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo
7. customThe residue was purified by chromatography on silica gel using
8. additiona mixture of hexanes:EtOAc (5:1)

ORD record

ord-f7bbed90c26a48bca4fae4915f5c924b

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07087601B2