Methyl 4-bromo-3-(tetrahydropyran-2-yloxy)benzoate → Benzenemethanol, 4-bromo-3-[(tetrahydro-2H-pyran-2-yl)oxy]-

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To a suspension of LiAlH4 (0.72 g, 19.04 mmol) in anhydrous Et2O (90 mL) was slowly added a solution of methyl 4-bromo-3-(tetrahydropyran-2-yloxy)benzoate (4.0 g, 12.69 mmol) in anhydrous Et2O (10 mL). The mixture was stirred at room temperature for 2 h and then cautiously quenched with Na2SO4.10H2O (until gas evolution ceases). The solids were filtered off and washed with Et2O (100 mL). The combined organic fractions were then dried (Na2SO4) and concentrated in vacuo. The pale yellow residue was purified by flash column chromatography [SiO2, Et2O/n-hexane (7:3)] to give 4-bromo-3-(tetrahydropyran-2-yloxy)benzyl alcohol as a colourless oil (3.21 g, 88%). δH (270 MHz, CDCl3) 1.54-1.76 (m, 3H), 1.82-2.12 (m, 3H), 3.54-3.64 (m, 1H), 3.8-3.94 (m, 1H), 4.61 (d, J=4.9, 2H), 5.52 (m, 1H), 6.85 (dd, J=7.9, 1.5, 1H), 7.13 (d, J=2.0, 1H), 7.49 (d, J=7.9, 1H), Nb. ArCH2OH too broad to be observed; LC-MS (APCI+): tR=3.84 min, m/z 306.11 (C12H1581BrO4+H3O+), 304.13 (C12H1579BrO4+H3O+); HPLC: tR=2.34 min (96%); HRMS (FAB+) Found 289.02646; C12H16O381Br requires 289.02624.

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