Boron tribromide → HCID 12133345, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3,5-diisopropyl-4-methoxyphenylacetate (100 mg) in dichloromethane (12 mL) at −78° C. was added a solution of boron tribromide (0.57 mL) in dichloromethane. The reaction mixture was stirred at −78° C. for 1 hour and at 0° C. for 1 hour, quenched by water, and extracted with dichloromethane. The combined organics were washed (brine), dried (MgSO4), filtered, and concentrated. Purification by preparative thin layer chromatography, with ethyl acetate:hexane:acetic acid (90:9:1) gave the title compound (24 mg); 1H-NMR (CDCl3) δ=1.25 (d, 12H, CH(CH3)2), 3.15 (m, 2H, CCH(CH3)2), 3.55 (S, 2H, CH2), 3.70 (S, 3H, OCH3), 6.98 (S, 2H, ArH)

Provenance & Evidence