Water → HCID 53995284, compound

Participants

Reaction Steps

To a solution of 3,5-dichloro-4-(methylsulfonyl)benzoic acid ethyl ester (2.6 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 water (2 mL) was added and the tetrahydrofuran was evaporated under vacuum. Toluene (100 mL) and water (30 mL) w ere added and then hydrogen peroxide (30% in water, 20 mL) was added at 10-20° C. After 30 min, the separated solid was dissolved by adding ethyl acetate (100 mL). The organic phase was separated and washed with saturated sodium pyrosulfite solution (25 mL) and then with potassium bicarbonate solution (1 M, 25 mL) and then dried with sodium sulphate and evaporated to dryness (yield 1.8 g). 1H-NMR (400 MHz, DMSO-d6) d=3.43 (s, 3H), 4.57 (s, 2H), 5.6 (b, 1H), 7.59 (s, 2H).

Provenance & Evidence