Pyridiniumtribromide → 7-Bromo-5-isobutyl-3,3-dimethyl-2,3-dihydro-benzofuran

Participants

Reaction Steps

To a solution of 5-isobutyl-3,3-dimethyl-2,3-dihydro-benzofuran (1.59 g, 7.78 mmol) in dichloromethane (40 mL) was added pyridinium tribromide (2.49 g, 7.78 mmol) and the reaction mixture stirred at room temperature overnight. The solution was washed with water and brine, dried (Mg2SO4), filtered and evaporated. The residue was purified on silica gel (0% to 2% ethyl acetate in hexane) to give 1.51 g of 7-bromo-5-isobutyl-3,3-dimethyl-2,3-dihydro-benzofuran (68%). 1H NMR (300 MHz; CDCl3): δ 0.90 (d, J=6.3 Hz, 6 H), 1.33 (s, 6 H), 1.77 (m, 1 H), 2.39 (d, J=7.5 Hz, 2 H), 4.30 (s, 2 H), 6.80 (d, J=1.5 Hz, 1 H), 7.05 (d, J=1.5 Hz, 1 H).

Provenance & Evidence