Boron tribromide → 4-(7,7-Dimethyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-8-yl)phenol

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Reaction Conditions

Reaction Steps

A solution of 3.30 mmol of 8-(4-methoxyphenyl)-7,7-dimethyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine in 50 ml of dichloromethane is admixed dropwise at 0-5° C. with 8.25 mmol of boron tribromide (1M solution in dichloromethane). The reaction solution is subsequently stirred at 0° C. for 1 hour, then admixed with saturated aqueous sodium hydrogen carbonate solution and extracted with dichloromethane (3×). The combined organic phases are dried over magnesium sulphate and evaporated. The residue is taken up in 0.5N NaOH and the mixture is extracted with ethyl acetate (3×). The combined organic phases are dried over magnesium sulphate and evaporated. The title compound is obtained as a beige solid and used without further purification for the next stage. Rt=4.91 (Gradient 1).

Provenance & Evidence