[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(N(CC)CC)C>C(OCC)C.O>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1To a solution of 4-bromomethylbenzenesulfonyl chloride (1.62 g, 6.01 mmol) in anhydrous diethyl ether (10 mL) at −10° C. was added a solution of morpholine (0.52 mL, 5.94 mmol) and triethylamine (0.92 mL, 6.6 mmol) in anhydrous diethyl ether (10 mL). The resulting mixture was allowed to warm up to room temperature over 1 hr, and continue stirring at r.t. overnight. The reaction mixture was then diluted with water, extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with water, brine, dried over Na2SO4, and filtered. Solvents were removed to yield an orange oil, which was purified on a 40 g silica gel column to give a white solid (1.34 g, 71% yield). 1H NMR (CD2Cl2) δ ppm: 7.75 (d, J=8.4 Hz, 2H), 7.63 (d, J=8.4 Hz, 2H), 4.58 (s, 2H), 3.77-3.73 (m, 2H), 3.03-2.98 (m, 2H). MS (ESI+): 320 (M+H)+.
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