Boron tribromide → HCID 17951868, compound

Participants

Reaction Steps

To a 50 ml round-bottom flask equipped with a magnetic stir-bar, an addition funnel and N2 inlet was added 4-(Bromomethyl)-5-[2-(4-methoxy-3-methylphenyl)ethyl]-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole (468 mg, 1.0 mmoles, 1 eq) and dry CH2Cl2 (15 ml, 0.1M). The mixture was cooled to −78° C. (dry ice/acetone) after which boron tribromide (1M in CH2Cl2, 3 ml, 3.0 mmoles, 3 eq) was added dropwise over the course of 15 minutes. After the addition was complete, the cold bath was removed and the reaction was allowed to warm to room temperature and stirred for 1 hour. After this time, the reaction was cooled to 0° C. and quenched very carefully with water. Once the reaction was quenched, it was transferred to a separatory funnel where the phases were separated. The aqueous fraction was washed three times with CH2Cl2 and the combined organic fractions were dried over Na2SO4, filtered, concentrated in vacuo to yield a quantitative yield of the titled phenol. The product was used without purification.

Provenance & Evidence