Water → 1-(2-Bromoethyl)-4-(methoxymethyl)benzene
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[H-].[Na+].[Br:3][CH2:4][CH2:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][CH:7]=1.I[CH3:15].O>C1COCC1>[CH3:15][O:11][CH2:10][C:9]1[CH:12]=[CH:13][C:6]([CH2:5][CH2:4][Br:3])=[CH:7][CH:8]=1[H-].[Na+].[Br:3][CH2:4][CH2:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][CH:7]=1.I[CH3:15].O>C1COCC1>[CH3:15][O:11][CH2:10][C:9]1[CH:12]=[CH:13][C:6]([CH2:5][CH2:4][Br:3])=[CH:7][CH:8]=1To a suspension of 60% NaH in paraffin (13.9 mmol; 0.56 g) in THF (20 ml) cooled to 0° C. was first added, dropwise, a solution of 4-(2-bromoethyl)benzyl alcohol (9.25 mmol; 1.99 g) in THF (20 ml) in an ice bath, followed by iodomethane (13.9 mmol; 1.972 g; 0.86 ml). The mixture was stirred at room temperature for 1 hour 30 minutes, after which it was poured into water and extracted with ethyl acetate. The combined organic phases were washed with saturated NaCl solution (3×20 ml), dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was chromatographed on a column of alumina, eluting with ethyl acetate, to give 1.38 g of product as an oil (65%).
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