C([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1)C1C=CC=CC=1.[C:18]([O-:21])([O-])=O.[K+].[K+].[Br:24][CH:25](Br)[CH3:26]>CN(C=O)C.CCOCC>[Br:24][CH2:25][CH2:26][O:14][C:11]1[CH:12]=[CH:13][C:8]([O:21][CH2:18][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:9][C:10]=1[N+:15]([O-:17])=[O:16]A mixture of 4-benzyl-2-nitrophenol (1.3 g, 5.3 mmol) and K2CO3 (1.2 g, 8.7 mmol) in DMF (10 mL) was stirred for 10 min. Dibromoethane (1.4 mL, 16.2 mmol) was added to the reaction mixture and heated at 70° C. for 24 hrs. The reaction mixture was diluted with ether (30 mL) and washed with water (20 mL) and brine (20 mL). The ether layer was dried (MgSO4) and concentrated under reduced pressure. The crude product was fractionated by flash chromatography (4:1 hexane/ethyl acetate) yielding bromoethane 6 as a yellow oil (1.3 g, 88%). 1H NMR: 3.65 (t, J=5 Hz, 2H), 4.35 (t, J=5 Hz, 2H), 5.05 (s, 2H), 7.0-7.5 (m, 8H).
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