Furan, 2-(bromomethyl)tetrahydro- → 2-(4-Chloro-benzyl)-tetrahydrofuran

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To a stirred mixture of (4-chlorophenyl)dihydroxyborane (524.0 mg, 3.351 mmol), 2-aminocyclohexanol hydrochloride (42 mg, 0.28 mmol) and nickel iodide (87.3 mg, 0.279 mmol) in i-PrOH (10.00 mL) was added sodium hexamethyldisilazane (1.075 g, 5.864 mmol) at 0° C. Then the mixture was stirred at rt for 5 min before 2-bromomethyl-tetrahydro-furan (460.00 mg, 2.80 mmol) was added by syringe. The resulting mixture was then stirred at 60° C. for 5 h. The solvent was then removed under reduced pressure and the resulting residue was purified by a flash chromatography(5% AcOEt in hexane).

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