[H-].[Na+].[Br:3][C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11][CH2:12][OH:13].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>O1CCCC1>[Br:3][C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1Sodium hydride (50% in oil) (1.7 g, 0.036 mol) was suspended in dry tetrahydrofuran (75 ml) in argon atmosphere. 2-(2-bromo-3-methylphenyl)-1-ethanol (7.0 g, 0.033 mol) solved in tetrahydrofuran (25 ml) was added dropwise during 30 min at room temperature. Benzyl bromide (6.2 g, 0.036 mol) was added and the reaction mixture was stirred at room temperature over night. Water (1.0 ml) was added carefully and the solvent was evaporated under reduced pressure. The residue was partitioned between water and diethyl ether and the water layer was extracted twice with diethyl ether. The ether extracts were combined, washed twice with water, and evaporated under reduced pressure. Purification of the residue by column chromatography on silica gel using heptane:methylene chloride (7:3) as eluent gave 7.5 g (74.3%) of the title compound.
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