Benzyl Bromide → 1-Benzyl-2-methyl-1H-indole-3-carboxylic acid

Participants

Reaction Steps

To a stirred solution of 0.50 g (3.10 mmol) 2-methyl-1H-indole-3-carboxylic acid (described in J. Heterocyclic Chem. 1977, 14, 1123) in 5 ml DMF were added 0.27 g (6.75 mmol) of NaH (60% in oil). The mixture was stirred at room temperature for 30 min. and then 0.39 ml (3.28 mmol) of benzyl bromid were added. The mixture was stirred for one additional hour and then poured onto water and extracted with ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Crystallization from Et2O afforded 1-benzyl-2-methyl-1H-indole-3-carboxylic acid.

Provenance & Evidence