Triethylamine → 1-(5-Bromo-4-chloro-2-fluoro-benzenesulfonyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline

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Reaction Steps

To 5-bromo-4-chloro-2-fluorobenzenesulfonyl chloride (3.15 g, 10.8 mmol) in dry DCM (40 mL), was added 4,4-dimethyl-1,2,3,4-tetrahydro-quinoline (1.50 g, 9.3 mmol) and triethylamine (2.15 mL, 15.5 mmol). The mixture was stirred at ambient temperature for 16 hrs. Additional sulfonyl chloride (0.93 g, 3.2 mmole) was added and the mixture was stirred an additional 72 hrs. The mixture was washed with 1N hydrochloric acid solution, saturated sodium bicarbonate solution and brine. The organic layer was dried over MgSO4 and the filtrate evaporated. The residue was purified by silica gel chromatography [eluent: 5% ethyl acetate in hexane] to give 1-(5-bromo-4-chloro-2-fluoro-benzenesulfonyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline as a yellow solid (3.6 g). tR=2.82 min (method 1).

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