1,3-Dibromo-5-fluorobenzene → HCID 69351008, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 1,3-dibromo-5-fluoro-benzene (19.8 g, 77.90 mmol) in dry diethyl ether (300 mL) and cool to −60° C. Add 1.6M n-BuLi in hexanes (50.9 mL, 81.44 mmol) dropwise over 15 min. and stir an additional 15 min. Add a pre-cooled (−60° C.) solution of 4-dimethylamino-cyclohexanone (10.0 g, 70.8 mmol) in diethyl ether (200 mL) dropwise over 30 min. Stir at −60° C. to −20° C. for 2 hr., then warm to ambient temperature and stir for 1 hr. Quench the reaction with water (200 mL) and extract with ethyl acetate (3×200 mL). Dry over sodium sulfate, filter and concentrate. Purify the residue by flash chromatography (15% 2M NH3/MeOH in DCM) to obtain 1-(3-Bromo-5-fluoro-phenyl)-4-dimethylamino-cyclohexanol as a white foam (14.5 g, 64.8%). MS (ES) m/z=316 (M−H)−, 318 (M+H)+; 1H NMR (CDCl3): δ 7.41 (d, 1H, J=2 Hz), 7.15 (m, 2H), 2.3 (m, 8H), 1.78 (m, 8H).

Provenance & Evidence