Boron tribromide → 2-(4-Chloro-6-fluoroquinazolin-2-yl)phenol

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Reaction Steps

A solution of 4-chloro-6-fluoro-2-(2-methoxyphenyl)quinazoline (3.0 g, 10.39 mmol) in CH2Cl2 (15 mL) was cooled to −78° C. To it was added a 1.0 M BBr3 solution in CH2Cl2 (52 mL, 52 mmol) dropwise. The reaction was allowed to warm to room temperature. It was neutralized with a saturated aqueous NaHCO3 solution, and the aqueous layer was extracted twice with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated. Purification via silica gel chromatography using 5-20% CH2Cl2/hexanes gave 2-(4-chloro-6-fluoroquinazolin-2-yl)phenol (1.68 g, 60%). LC/MS: m/z 275.3 (M+H)+ at 3.39 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Provenance & Evidence