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, 17 mmol). The reaction mixture was stirred at 90° C. for 1 h, cooled to rt and quenched with brine (50 mL). After extraction with EtOAc (3×100 mL), the organic layers were combined, washed with brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, hexanes:EtOAc 5:1) to afford 4-bromo-2-fluoro benzyl cyanide as yellow solid. MS (ESI) 307 (M+H)+.

1. temperaturecooled to rt
2. customquenched with brine (50 mL)
3. extractionAfter extraction with EtOAc (3×100 mL)
4. washwashed with brine (50 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by flash chromatography (silica gel, hexanes:EtOAc 5:1)

ORD record

ord-bdc28b5ce6e24691832732f0a37423ba

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07087601B2