Boron tribromide → HCID 18432940, compound

Participants

Reaction Steps

To a −78° C. solution of 4-chloro-6-methoxy-2-phenyl-quinoline (1.0 g, 3.7 mmol) in CH2Cl2 (25 ml) was added dropwise BBr3 (11.1 ml, 11.1 mmol, 1M in CH2Cl2). Reaction mixture was then allowed to warm to room temperature. After 4.5 hours, mixture was cooled to −10° C. and quenched slowly with a saturated solution of NaHCO3 (70 ml). The aqueous phase was extracted with ethyl acetate (3×100 ml). Combined organic phases were dried over Na2SO4 and concentrated. The solid residue was refluxed during 1 hour in ethyl acetate (30 ml), cooled to room temperature, and filtered. Filtrate was concentrated and chromatographed over silica gel (hexane-ethyl acetate, 4:1) to provide 4-chloro-2-phenyl-quinolin-6-ol (0.375 g, 40%) as a yellow solid, m. p. 180-181° C., MS: m/e=255 (M+).

Provenance & Evidence