Hexachloroethane → 2-Chloro-3-fluorobenzoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 3-fluorobenzoic acid (8.0 g, 64.3 mmol) in 40 mL of THF was added dropwise to a solution of sec-butyllithium (90 mL, 128.6 mmol) and N,N,N′,N′-tetramethylethylenediamine (20.0 mL, 147.9 mmol) in THF (100 mL) at −90° C. After addition, the reaction mixture was stirred at −90° C. for 30 minutes. Hexachloroethane (54 g, 257.2 mmol) in THF (100 mL) was added to reaction mixture dropwise. Then the reaction mixture was stirred at −78° C. to room temperature for 16 hours. The solvent was evaporated and the water was added to the residue. The reaction mixture was acidifed to PH=1 by added conc. hydrochloric acid. Then the reaction mixture was extracted with ether (3×). The combined organic phase was dried and conc. The crude product was washed with hexane for 3 times. Then it was filtered to get pure product (9.2 g, 93%). EI-MS m/z 172.89 (M−).

Provenance & Evidence