Boron tribromide → HCID 23594017, compound

Participants

Reaction Steps

Boron tribromide (0.148 mL, 1.56 mM) was slowly added to a stirred solution of 5-benzyl-11-methoxy-5H-benzo[b]carbazole-1-carboxylic acid, methyl ester, (0.474 g, 1.2 mM) in 8 mL methylene chloride at −10° C. After 1.5 h, the mixture was quenched with methanol (1.22 mL, 30.0 mM) and allowed to warm to room temperature with stirring over 2 h. The mixture was diluted with methylene chloride, washed with H2O, 1N HCl, saturated aqueous NaHCO3 solution, and saturated brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resultant orange-brown solid was purified by column chromatography on silica gel (elution with gradient hexane/ethyl acetate) to afford 0.245 g (47%) of the title compound 5-benzyl-11-hydroxy-5H-benzo[b]carbazole-1-carboxylic acid, methyl ester as an orange foam (MW 381.44).

Provenance & Evidence