6-bromo-1H-indole-2-carboxylic acid → (6-Bromo-1H-indol-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

6-Bromo-1H-indole-2-carboxylic acid (2.4 g, 10 mmol) was dissolved in THF (20 mL) and cooled to 0° C. Lithium aluminum hydride (20 mmol, 1 M in THF) was added to the solution via syringe. The mixture was stirred overnight at room temperature. The excess reagent was quenched with the slow addition of aqueous KOH (10 mL, 1 M). The mixture was stirred vigorously for 30 min. The mixture was filtered through Celite. The filtrate was concentrated and chromatographed (0-20% EtOAc in CH2Cl2) to afford the product as a yellow powder (1.87 g, 83%). LC-MS 224.1, 226.1 [M+H]+, RT 1.03 min.

Provenance & Evidence