Sulfuric Acid → 8-Bromochroman-3-ol

Participants

Reaction Steps

Tl2O3 (2.38 g, 5.2 mmol) was added at room temperature to a mixture of H2SO4 (6.9 ml) and water (6.1 ml) and this mixture was stirred for 30 min and added to o-allyloxy-bromo-benzene (1.9 g, 8.92 mmol) and water was added (37 ml). The reaction mixture was stirred in 60° C. under Argon. The product was extracted with CH2Cl2 and the organic layer was washed with water, dried (Na2SO4), filtered and the solvent was removed under reduced pressure to give 1.34 g of a raw oil, which was chromatographed (SiO2 and ether as eluant). The fractions containing at least 85% purity of the product were pooled and the solvent was removed, yielding 310 mg of an oil. GC/MS showed M+ /M+2 at m/e=228.00(100%)/230.00(88%).

Provenance & Evidence