Benzyl Bromide → 2-(Benzyloxy)-1-methoxy-4-nitrobenzene

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[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:13]([O:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

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실험 절차

A solution of 2-methoxy-5-nitrophenol (54.3 g, 321 mmol), benzyl bromide (26.5 mL, 223 mmol,) and cesium carbonate (73 g, 223 mmol) is stirred in N,N-dimethylformamide (250 mL) for 24 h at room temperature. The mixture is partitioned between water and ethyl acetate. The layers are separated and the organic layer washed three times with water, once with brine, dried (sodium sulfate), filtered and evaporated to give a crude solid. The crude product is recrystallized from ethyl acetate to yield the title compound, 56.4 g (68%), as a white crystalline solid.