Boron Trichloride → 4-Chloroquinazolin-8-ol

Participants

Reaction Steps

A solution of boron trichloride in dichloromethane (1.0 molar, 46.0 mL) is added via syringe to a solution of 4-chloro-8-methoxyquinazoline (2.24 g, 11.5 mmol) in chloroform, under a nitrogen atmosphere. The reaction mixture is heated at reflux for 1/2 hour, cooled to room temperature and diluted with a mixture of ice and saturated sodium bicarbonate solution. The phases are separated and the aqueous phase is extracted with chloroform. The organic phases are combined, washed with a 10% ethylenediaminetetraacetic acid (EDTA) solution, dried over MgSO4 and concentrated in vacuo to obtain the title product as a white solid, 1.93 g (93%), mp>252° C.

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