Hydrochloric Acid → 1,3-Dichloro-2-(2,3-difluorophenyl)propan-2-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-bromo-2,3-difluorobenzene (19.5 g, 0.10 mol) in dry diethyl ether (120 mL), under nitrogen at −78° C., was added dropwise, n-hexyllithium (2.3 M in hexane, 41.7 ml, 0.096 mol). The mixture was stirred for 1 min after which a solution of 1,3-dichloroacetone (12.2 g, 0.096 mol) in dry diethyl ether (30 mL) was added dropwise. The resulting mixture was stirred at −78° C. for 1 h and then brought to ambient temperature and stirred for 1 h. Aqueous hydrochloric acid (50 mL. 10%) was added and the mixture was extracted with ethylacetate (2×50 ml). The combined organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to dryness. The crude product was purified by flash column chromatography on silica gel (ethylacetate/isooctane, 1:9 to 1:1) to give the title compound (11.8 g, 48%). MS m/z (rel. intensity, 70 eV) 241 (M+, 1), 193 (33), 191 (bp), 141 (11), 127 (68).

Provenance & Evidence