Benzyl mercaptan → 5-(Benzylthio)-2-fluorobenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 5-bromo-2-fluorobenzonitrile (10 g, 50 mmol) in toluene (250 mL) was added N,N-diisopropylethylamine (26 mL, 150 mmol), benzyl mercaptan (5.87 mL, 52 mmol) and dichloro[1,1′ bis(di-tert-butylphosphino)]ferrocene palladium (II) (500 mg, 1 mmol). The reaction mixture was heated at 60° C. for 16 hours. The reaction mixture was diluted to 500 mL volume with ethyl acetate and washed with dilute brine (300 mL), then 2N HCl (2×300 mL) and finally dilute brine (300 mL). The combined organic layers were dried over MgSO4, filtered and the solvent removed in vacuo. The residue was purified using silica gel column chromatography eluting with 10% ethyl acetate in heptane to afford the title compound as light brown solid (6.18 g, 51%)

Provenance & Evidence