Dimethylformamide → 2-Fluoro-4-methylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

Under N2, to a suspension of 1-bromo-2-fluoro-4-methyl-benzene (2.59 g, 13.7 mmol) and Zn(CN)2 (1.60 g, 13.7 mmol) in dry DMF (50 mL) was added 1,1′-bis(diphenylphosphino)ferrocene (DPPF) (0.0753 g, 0.136 mmol) and Pd2(dba)3 (dba=di(benzylidene)acetone) (0.0623 g, 0.0681 mmol). After the mixture was heated at 130° C. for 2 days, the solvent was removed by evaporation under vacuum, and saturated aqueous NaHCO3 (40 mL) was added. The aqueous suspension was extracted with CH2Cl2 (3×40 mL), and the extract was dried over Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residual solid was purified by flash chromatography on silica gel (1:20 EtOAc/hexanes), affording 2-fluoro-4-methyl-benzonitrile as a pale yellow solid (1.21 g, 65%). 1H NMR (CDCl3) δ 2.43 (s, 3H), 7.01-7.07 (m, 2H), 7.48-7.52 (m, 1H).

Provenance & Evidence