Water → 4-Chloro-3-(methylsulfonyl)benzenemethanol

Participants

Reaction Steps

To a suspension of 4-chloro-3-(methylsulfonyl)benzoic acid methyl ester (2.4 g) in tetrahydrofuran (50 mL) was added lithium triethylborohydride (1 M in tetrahydrofuran, 24 mL) at 0-5° C. under nitrogen. The mixture was stirred for 30 min and then more of lithium triethylborohydride (1M in tetrahydrofuran, 5 mL) was added and the mixture was further stirred for 60 min. Water (2 mL) was added and the tetrahydrofuran was evaporated under vacuum. Toluene (100 mL) and water (30 mL) were added and then hydrogen peroxide (30% in water, 20 mL) was added at 10-20° C. After 30 min the organic phase was separated and washed with potassium bicarbonate solution (1 M) and then dried with sodium sulphate and evaporated to dryness (yield 1.2 g). 1H-NMR (400 MHz, DMSO-d6) d=3.36 (s, 3H), 4.59 (d, J=5.7 Hz, 2H), 5.52 (t, J=5.7 Hz, 1 H), 7.66 (dd, J=8.2 Hz, 2.1 Hz, 1H), 7.70 (d, J=8.2 Hz, 1H), 8.03 (d, J=2.1 Hz, 1H).

Provenance & Evidence