Carbon Tetrachloride → 1-Benzyloxy-3-chloromethyl-7-fluoro-2-methyl-naphthalene

Beteiligte Stoffe

Reaktionsschritte

A three-neck round-bottom flask was charged with triphenylphosphine (23.33 g, 88.34 mmol), tetrahydrofuran (70 mL), and carbon tetrachloride (35 mL, 0.36 mol) under an argon atmosphere. The resulting mixture was stirred at room temperature for 20 minutes. A solution of (4-benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-methanol (13.09 g, 44.17 mmol) in tetrahydrofuran (50 mL) was added rapidly to the reaction mixture via an addition funnel. The reaction mixture was heated at reflux for 1 hour. The reaction mixture was cooled to room temperature, and the solvents were removed in vacuo. The residue was diluted with water, and the resulting mixture was extracted twice with ethyl acetate. The organic phases were washed twice with water, and the resulting aqueous layers were extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated. The crude product was purified using flash chromatography (Analogix SuperFlash™ column, 10-25% dichloromethane in hexane), affording 10.8 g (77%) 1-benzyloxy-3-chloromethyl-7-fluoro-2-methyl-naphthalene as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.02 (dd, J=8.9, 5.9 Hz, 1 H), 7.89 (s, 1 H), 7.53-7.65 (m, 3 H), 7.35-7.50 (m, 4 H), 4.97 (s, 4 H), 2.47 (s, 3 H).

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