[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.C(=O)(O)[O-].[Na+]>ClCCl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][O:5][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][O:10]1
Pyridinium p-toluenesulfonate (0.30 g, 0.0012 mol) was added to a solution of 2-bromobenzyl alcohol (25 g, 0.134 mol) in dichloromethane (100 ml), and the mixture was stirred at room temperature. To this mixture was added 3,4-dihydro-2H-pyrane (16.86 g, 0.20 mol). After the resulting mixture was stirred at room temperature for 2 hours, a saturated aqueous solution (200 ml) of sodium bicarbonate was added. The mixture was extracted with dichloromethane (200 ml). After the mixture was dried over anhydrous magnesium sulfate, the solvent was evaporated to obtain the desired compound 1-bromo-2-(2-tetrahydropyranyloxymethyl)benzene (36.00 g, Yield: 99.3%) as an oil.
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