Methanol → 5-Hydroxy-2,3-dihydro-1H-isoindol-1-one

Participants

Reaction Steps

A mixture of 5-methoxy-2,3-dihydro-isoindol-1-one (3.7 g, 23 mmol) and boron tri-bromide (1 M in CH2Cl2, 15.2 mL, 88 mmol) in CH2Cl2 (30 mL) at −78° C. was stirred for 16 h at RT. The mixture was then cooled to −78° C. and MeOH (25 mL) was added. After 1 h at −78° C. the mixture was evaporated and the residue purified by chromatography (SiO2, CH2Cl2:2N NH3-MeOH 98:2 to 90:10) to afford the title product (2.5 g, 72%) as an off-white solid. MS m/e=148.0 (M−H+).

Provenance & Evidence