[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:13]I>CN(C)C=O>[CH3:2][CH2:3][CH2:4][CH:5]([CH3:8])[CH3:6].[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:10][CH3:13])[CH3:9])=[CH:4][CH:3]=1Dissolve 1-(4-bromo-phenyl)-ethanol (0.79 mL, 6.62 mmol) in dry N,N-dimethylformamide (7 mL) at ambient temperature under nitrogen atmosphere. Add sodium hydride (60% dispersion in oil, 397 mg, 9.93 mmol), stir the reaction for 30 min., then add methyl iodide (0.50 mL, 7.94 mmol) and stir the reaction for a further 23 hr. under nitrogen. Quench with water (30 mL), extract with DCM (3×30 mL), pass through an IST Phase Separator Frit® and concentrate. Purify using silica gel chromatography, eluting with 0:100 to 20:80 ethyl acetate: isohexane to give 1-bromo-4-(1-methoxy-ethyl)-benzene as a clear oil (1.39 g, 98%). 1H-NMR (400 MHz, CDCl3) δ 7.47 (d, 2H), 7.20 (d, 2H), 4.25 (q, 1H), 3.21 (s, 3H), 1.40 (d, 3H).
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