To a mixed solution of 2-bromoethanol (3.8 g, 30.0 mmol) and 3,4-dihydro-2H-pyran (2.5 g, 30.0 mmol) dissolved in dichloromethane (50 mL), p-toluenesulfonic acid (380.0 mg, 2.2 mmol) was added in portions. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the mixture was concentrated and purified by silica gel column chromatography (petroleum ether/ethyl acetate, 50:1) to afford 2-(2-bromoethoxy)tetrahydro-2H-pyran (5.6 g, yield: 89%) as a colorless oil.
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