[F:1][C:2]1[CH:3]=[C:4]([CH2:18]O)[CH:5]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:7]=1.[Br-:20].[Br-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl.CC(=O)OCC>[Br:20][CH2:18][C:4]1[CH:5]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:7]=[C:2]([F:1])[CH:3]=1A mixture of [3-fluoro-5-(4-methoxy-benzylamino)-phenyl]-methanol (522 mg, 2 mmol) and triphenylphosphine dibromide (1.27 g, 3 mmol) in dichloromethane (6 ml) was stirred in an ice bath for 30 min. The mixture was then warmed up to room temperature, diluted with EA (20 ml), washed with saturated aqueous sodium bicarbonate solution followed by brine, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, EA:hexane (1:10)) to afford 570 mg (88%) of a pale yellow syrup. 1H NMR (200 MHz, CDCl3) δ 3.86 (3H, s), 4.30 (2H, s), 4.40 (2H, s), 6.41 (1H, m), 6.56-6.60 (2H, m), 6.90-6.96 (2H, m), 7.31-7.35 (2H, m).
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