O[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:14][CH2:15][CH3:16])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].C(Br)(Br)(Br)[Br:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:22][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:14][CH2:15][CH3:16])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]To a solution of methyl 3-(hydroxymethyl)-5-[(methylsulfonyl)(propyl)amino]benzoate (2.99 g, 9.92 mmol) in dichloromethane (90 mL) were added carbon tetrabromide (4.28 g, 12.9 mmol) and triphenylphosphine (3.12 g, 11.9 mmol). After 15 h, the reaction mixture was concentrated in vacuo and purified by flash chromatography (silica, 0-40% EtOAc/hexanes) to provide methyl 3-(bromomethyl)-5-[(methylsulfonyl)(propyl)amino]benzoate as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.04 (s, 1H), 7.91 (s, 1H), 7.61 (s, 1H), 4.50 (s, 2H), 3.94 (s, 3H), 3.67 (t, J=7.2 Hz, 2H), 2.90 (s, 3H), 1.56-1.46 (m, 2H), 0.92 (t, J=7.3 Hz, 3H).
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