Bromine → 1-Benzyl-1h-indole-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide

Participants

Reaction Steps

A solution of bromine (0.37 mL, 0.7134 mmol) in 60 mL glacial acetic acid was added dropwise under nitrogen over 2 h to a solution of 1-benzyl-1H-indole-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (3.0 g, 0.713 mmol), prepared in the previous step, in 300 mL glacial acetic acid at room temperature. The reaction stirred for 18 h (overnight). The solvent was removed under reduced pressure. The resulting residue was diluted with ethyl acetate and extracted with 5% sodium bicarbonate. A solid precipitated from the organic layer and was collected by filtration. The filtrate was dried (MgSO4) and concentrated under reduced pressure to give a tan solid. The two solids were combined and taken up in a mixture of ethyl acetate and isopropanol. A certain amount of material (1.0 g) would not dissolve upon heating and was removed by filtration. The filtrate was allowed to cool and upon cooling crystals formed. The crystals were collected by filtration and dried under reduced pressure to give 1-benzyl-1H-indole-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (0.766 g, 22%) as a tan solid, mp 181-182° C.

Provenance & Evidence