Water → 1-(5-bromo-4-chloro-2-fluoro-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine

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Reaction Steps

To a solution of DCM (20 mL) containing 5-bromo-4-chloro-2-fluoro-benzenesulfonyl chloride (2.82 g, 9.2 mmol) was added 2,3,4,5-tetrahydro-1H-benzo[b]azepine (1.35 g, 9.2 mmol) and triethylamine (2.8 mL, 21 mmol). The mixture was stirred for 16 hrs. The mixture was then diluted with 50 mL of DCM and repartioned with 50 mL of water. The organic layer was further washed with water (2×30 mL) and dried over MgSO4. Concentration and purification by silica gel column chromatography eluting with hexane/ethyl acetate (9/1 to 6/1) yielded 1-(5-bromo-4-chloro-2-fluoro-benzenesulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine as the pale yellow solid (2.70 g). NMR (CDCl3), δ, 8.059 (1H, d, J=7.2 Hz), 7.404 (1H, d, J=9.3 Hz), 7.202-7.218 (2H, q), 7.073-7.129 (1H, m), 7.860 (1H, d, J=7.8 Hz), 3.746 (2H, m), 2.750-2.813 (2H, m), 1.906-1.982 (2H, m), 1.639-1.678 (2H, m).

Provenance & Evidence