5-Bromo-3-indoleacetic acid → 5-Bromo-1H-indole-3-ethanol

Participants

Reaction Steps

To a stirred solution of 5-bromoindole-3-acetic acid (1.9 g., 7.48 mmol., 1 eq.) in dry THF (17 mL.) at 0° C. was added lithium aluminum hydride (570 mg. 14.96 mmol., 2 eq.) portionwise over 30 minutes. The reaction mixture coagulated. THF (20 mL.) was added and the cooling bath was removed. The mixture was stirred vigorously. Let stir overnight. The reaction mixture was carefully quenched with 1N aqueous HCl and then acidified with 2N aqueous HCl. The mixture was filtered through Celite™ and the Celite™ was washed with THF. The filtrate was concentrated in vacuo, dissolved in EtOAc, and washed with water. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. TLC analysis of the residue showed unreacted starting material. The residue was dissolved in Et2O and extracted with 0.25N aqueous NaOH. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo giving 1.16 g 5-bromo-3-hydroxyethylindole.

Provenance & Evidence