Boron tribromide → HCID 23594016, compound

Participants

Reaction Steps

Boron tribromide (0.3 mL, 3.0 mM) was slowly added to a stirred solution of 5-benzyl-11-methoxy-7,8,9,10-tetrahydro-5H-benzo[b]carbazole-1-carboxylic acid, methyl ester, (0.12 g, 0.3 mM) in 5 mL methylene chloride at −10° C. After 5.5 h, the mixture was quenched with methanol (3.0 mL, 75.0 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 to afford 0.108 g (93%) of the title compound 5-benzyl-11-hydroxy-7,8,9,10-tetrahydro-5H-benzo[b]carbazole-1-carboxylic acid, methyl ester as a yellow solid (MP 174–176° C., MW 385.47).

Provenance & Evidence