Boron tribromide → HCID 17898073, compound

Participants

Reaction Conditions

Reaction Steps

To 3,5-dimethyl-4-(3'-isopropyl-4'-methoxybenzyl) anisole (8) (1.3 g, 4.35 mmol) in 75 mL of methylene chloride at -78° C. was added 44 mL of boron tribromide 1.0M in methylene chloride). The reaction mixture was stirred for 30 min at -78° C. and for 10 hours at room temperature. The reaction mixture was washed with water (2×100 mL), dried (MgSO4), and evaporated to give crude product (1.5 g). Purification using flash column chromatography (silica gel, 80:20 hexane/ethylacetate) gave 3,5-dimethyl-4-(4'-hydroxy-3'-isopropylbenzyl) phenol (9) (812 mg, 3.00 mmol, 69%); 1HNMR (CDCl3) δ 1.2 (d, 6H), 2.23 (s, 6H), 3.15 (heptet, 1H), 3.87 (s, 2H), 6.58 (m, 4H), 6.92 (s, 1H).

Provenance & Evidence