[Br:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]([CH2:10][C:11]([OH:13])=O)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.O=S(Cl)Cl.[C:20]1([O:26][CH3:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl.CO.CN(C=O)C>[Br:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]([CH2:10][C:11]([C:23]2[CH:24]=[CH:25][C:20]([O:26][CH3:27])=[CH:21][CH:22]=2)=[O:13])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1
To a cooled (0° C.) solution of 55 (2.8 g, 10 mmol) in CH2Cl2 (50 ml) was added SOCl2 (1.8 g, 15 mmol) and DMF (2 ml) and the reaction was stirred for 3 hr. The solution was concentrated and the resulting oil was taken up into dichloroethane (50 ml). The solution was cooled and anisole (2.0 g, 1 8.4 mmol) was added followed by AlCl3 (1.8 g, 13.8 mmol). The reaction was stirred for 1 hr and was then quenched with 2N HCl aq. The organic layer was dried over MgSO4, concentrated to give an oil which was taken up into MeOH and a solid crystallized. The solid was collected by filtration to give a white solid (2.3 g, 63%); Mp=91–93° C.; 1H NMR (DMSO-d6) δ 8.01 (d, 2 H, J=8.4 Hz), 7.10–7.05 (m, 3 H), 6.85 (d, 1 H, J=5.7 Hz), 4.35 (s, 2 H), 3.85 (s, 3 H), 3.72 (s, 3H), 3.59 (s, 3 H); MS 363/365 (M−H)−
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