Diisobutylaluminum hydride → 5-Bromo-4-methyl-1,3-dihydroisobenzofuran-1-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-4-methylisobenzofuran-1(3H)-one (3.45 g, 15.19 mmol) in toluene (100 mL) at −78° C. was added DIBAL-H (21.27 mL, 21.27 mmol) dropwise. After stirring at −78° C. for 2 h, the reaction was quenched by methanol at −78° C., then warmed to rt, then 20 mL of saturated sodium sulfate was added and the mixture was vigorously stirred at rt for 30 min. Next, the mixture was filtered and washed with ethyl acetate. The filtrate was washed with saturated sodium bicarbonate, dried over sodium sulfate, then concentrated to give the title compound. LC/MS: (M−17)+: 210.92; 212.91.

Provenance & Evidence