[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][C:3]=1[CH2:16]O.P(Br)(Br)[Br:19].C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:10]1([CH2:9][O:8][C:6]2[CH:5]=[CH:4][C:3]([CH2:16][Br:19])=[C:2]([CH3:1])[CH:7]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1To a solution of {2-methyl-4-[(phenylmethyl)oxy]phenyl}methanol (1.49 g, 6.53 mmol) in DCM (20 ml) under nitrogen in an ice-water bath was added a solution of phosphorus tribromide (0.62 ml, 6.57 mmol, Aldrich) in DCM (10 ml). The solution was allowed to warm to ambient temperature and stirred for 3 h. The reaction mixture was poured onto ice-water (70 ml) and saturated aqueous sodium hydrogen carbonate (30 ml). The mixture was diluted with DCM (50 ml) and the phases separated. The aqueous extract was washed with dichloromethane DCM (20 ml). The combined organic extracts were washed with water (50 ml), dried (MgSO4), filtered and the solvent removed in vacuo to leave 4-(bromomethyl)-3-methylphenyl phenylmethyl ether as a yellow oil (1.72 g).
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