[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.CC(C)=O>[CH2:12]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1A solution of 4-Bromo-3-nitrophenol (1.0 g, 4.6 mmol) and benzyl bromide (0.82 mL, 7 mmol) in acetonitrile (30 mL) and acetone (15 mL) was treated with K2CO3 (970 mg, 7 mmol). The resulting mixture was heated at reflux under nitrogen for 17 h. The reaction mixture was evaporated in vacuo and the residue was dissolved in 40 mL ethyl acetate. The solution was filtered under vacuum then the filtrate was washed successively with distilled water (30 mL ), 1M HCl solution (30 mL×3), brine (30 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was chromatographed over 100 g of silica gel using 3:1 mixture respectively of hexanes and ethyl acetate to give the benzyl alcohol in 95% yield; 1H NMR(CDCl3) δ5.11(2H, s), 7.02(1 H, dd, J1=2.9, J2=8.9), 7.41(5H, m), 7.46(1 H, d, J=2.9), 7.60(1H, d, J=8.9); 13C NMR(CDCl3) δ71.4, 105.4, 112.4, 121.1, 128.1, 128.9, 129.1, 129.3, 129.5, 135.8, 136.0, 138.2, 158.7; HRMS calcd for C13H10NO3Br: 306.9844; found: 306.9846.
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