Water → HCID 13922868, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 5-methoxymethyl-2-sulfamoylbenzo[b]thiophene, (7.4 g, 0.029 mol) in 300 ml of dry methylene chloride cooled to -30° C. was added boron tribromide (30 ml of a 1M solution in methylene chloride, 0.03 mol) over a 20 minute period. The resulting solution was stirred for 11/2 hours as the temperature rose to ambient. The solution was cooled to 0° C. and there was added dropwise 150 ml of water keeping the temperature below 20° C. The methylene chloride layer was separated and the aqueous suspension was extracted with three portions (200 ml) of methanol-chloroform (50/50). The combined extracts were washed with ice water, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give 8.8 g of tan solid (quantitative yield of crude product) which after recrystallization from 1,2-dichloroethane had m.p. 171°-173° C.

Provenance & Evidence