Hydrochloric Acid → 4-Acetyl-2-fluorobenzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 5.0 g (0.02 mol) 4-bromo-2-fluorobenzonitrile, 6 ml TEA, 906 mg (0.0022 mol) dppp, 5.8 g (0.04 mol) TIOAc, and 448 mg (0.002 mol) Pd(OAc)2 in 50 ml DMF was deaired under a stream of N2. The mixture was heated to 90° C. for 7 hours. The reaction was cooled to room temperature and 25 mL 2N HCl was added and stirred to 30 minutes. The mixture was poured into 300 ml water and extracted with Et2O (2×300 mL). The combined organics were washed with water (2×80 mL), brine (1×80 mL), dried over MgSO4 and concentrated to give an oil, which was then chromatographed on silica gel eluted with 30% ethyl acetate/70% hexanes to give 2.5 g of a yellow/orange oil.

Provenance & Evidence