[NH2:1][CH2:2][C:3]([C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1)([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)[OH:4].C(N(CC)CC)C.[Cl:27][CH2:28][C:29](Cl)=[O:30].O>C1(C)C=CC=CC=1.CCOC(C)=O>[Br:19][C:16]1[CH:15]=[CH:14][C:13]([C:3]([OH:4])([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=2)[CH2:2][NH:1][C:29](=[O:30])[CH2:28][Cl:27])=[CH:18][CH:17]=1
To a solution of 2-amino-1-(4-bromo-phenyl)-1-(3-methoxy-phenyl)-ethanol (0.94 g, 2.92 mmol) in toluene (10 mL) at 0° C. was added triethylamine (0.41 mL, 3.07 mmol). To the reaction mixture was added a solution of chloroacetylchloride (0.23 mL, 2.92 mmol) in toluene (1 mL) and the reaction was stirred at 0° C. for 30 min. and at room temperature for 1 h. To the reaction was added cold water (10 mL) and the mixture was stirred for 10 min. EtOAc was added (20 mL) and the layers were separated. The aqueous layer was washed with EtOAc (2×20 mL) and the combined organic extracts were dried over MgSO4, and concentrated. Purification by flash chromatography with hexanes/EtOAc (4:1) afforded 1.08 g of N-[2-(4-bromo-phenyl)-2-hydroxy-2-(3-methoxy-phenyl)-ethyl]-2-chloro-acetamide. 1HNMR (400 MHz, CDCl3) δ 7.45-7.41 (comp, 2H), 7.29-7.20 (comp, 3H), 6.97-6.96 (m, 1H), 6.93-6.90 (m, 1H), 6.86-6.85 (m, 1H), 6.85-6.79 (m, 1H), 4.14-3.98 (comp, 2H), 3.95 (s, 2H), 3.77 (s, 3H), MS (M+1) 380.0, 382.0.
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