p-Bromobenzenesulfonyl chloride → Methyl 5-[[(4-bromophenyl)sulfonyl](hexyl)amino]-2-fluorobenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-fluoro-5-(hexylamino)benzoate (800 mg; 3.16 mmol) in anhydrous DCM (50 mL) were added 4-bromobenzenesulfonylchloride. (807 mg; 3.16 mmol) and TEA (0.53 mL). The reaction mixture was stirred overnight at 25° C. under N2 atmosphere. Then the mixture was poured into a saturated solution of NaHCO3 and extracted with DCM (2×200mL). The combined organic layers were washed with a saturated solution of NH4Cl followed by brine, dried over magnesium sulfate, filtrated and the solvent was removed under reduced pressure to give a brown cream. Purification by flash chromatography using silicagel (c-Hex/EtOAc, 95:5 then 90:10):gave 1.0 g (67.4%) of the title compound as a colorless cream. HPLC, Rt: 5.23 min (purity=97.13%). LC/MS,. M+(ESI): 272.1. 1H NMR (CDCl3) δ: 7.63 (m, 2H), 7.52 (m, 1H), 7.43 (d, J=9.2 Hz, 2H), 7.25 (m, 2H), 7.13 (t, J=9.2 Hz, 1H), 3.91 (s, 3H), 3.49 (t, J=6.97 Hz, 2H), 1.25 (m, 8H), 0.85 (t, J=6.8 Hz, 3H).

Provenance & Evidence