Diisobutylaluminum hydride → (5-bromo-1-methyl-1H-indol-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 5-bromo-1-methyl-1H-indole-2-carboxylate (ca. 9.0 g) in CH2Cl2 (80 mL) was added DIBAL-H (1.0M in hexanes, 70.0 mL, 2.2 eq) at −78° C. over 15 min. The reaction was monitored by LC-MS. After stirring for 1 h at −78° C., the reaction was quenched with 1N HCl (20 mL) at −78° C. then allowed to warm to room temperature and stirred for additional 30 min to break aluminum emulsion. The biphasic mixture was extracted by ether/EtOAc (1:1, 3×50 mL). The combined organic layers were dried over Na2SO4 then concentrated to give (5-bromo-1-methyl-1H-indol-2-yl)methanol (ca. 7.8 g, quant.) which was used in the next step without further purification.

Provenance & Evidence