Boron tribromide → 4-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile

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Reaction Steps

Boron tribromide (1M in DCM, 262 ml) was added to a solution of 4-(4-methoxyphenyl)-tetrahydro-2H-pyran-4-carbonitrile (14.7 g, 67.9 mmol) in DCM (294 ml) at 0° C. under N2 keeping the temperature below 5° C. The reaction was allowed to warm to room temperature and stirred for 48 hours. The mixture was cooled to −10-0° C. with dry ice acetone and quenched with saturated aqueous sodium bicarbonate (294 ml). The mixture was allowed to warm to room temperature and stirred for 1 hour. The mixture was separated and the aqueous extracted with DCM (3×250 ml). The combined organic extracts were dried over MgSO4, filtered, washed with DCM and concentrated in vacuo to give the title compound (10.8 g, 78%).

Provenance & Evidence