Hydrogen Peroxide → HCID 66892729, compound

Participants

Reaction Steps

A solution of 2-phenyl-7-[(trifluoromethyl)thio]-4H-1,3,2-benzodioxaborinin (14.0 g, 44 mmol) and H2O2 (30% in water, 27.0 ml, 264 mmol) in THF (100 ml) was stirred at ambient temperature for 3 h, before it was quenched at 0° C. with a aquous solution of Na2SO3 (19.0 g). The mixture was acidified with HCl (10%), extracted with EtOAc and the combined organic layers were evaporated to dryness (no drying agent). The crude product was purified on flash column chromatography (isooctane/EtOAc 4:1 and isooctane/EtOAc 7:3) to afford two different fractions. One fraction with the stereoisomer as a by-product, 2-(hydroxymethyl)-3-[(trifluoromethyl)thio]phenol (4.1 g) and one with the title product (2.75 g). 1H-NMR (400 MHz, MeOH): δ 7.40 (1H, d, J 8.0 Hz), δ 7.13 (1H, d, J 8.0 Hz), δ 7.12 (1H, s), δ 4.66 (2H, s).

Provenance & Evidence