2-(2-Bromophenyl)-2-propanol

917-64-6

6091-64-1

7073-69-0

To a solution of 26.50 g (0.14 mol) of ethyl 2-bromobenzoate (4a) dissolved in 35 mL of anhydrous diethyl ether at -5°C was slowly added methylmagnesium iodide Grignard's reagent prepared from 9.1 g (0.37 mol) of magnesium and 53.3 g (0.37 mol) of freshly distilled methyl iodide in 85 mL of anhydrous ether. Upon completion of the reaction, the reaction was quenched by the addition of 38% ammonium chloride solution (58 mL). The ether layer was separated by decantation and the remaining pasty precipitate was extracted with ether (3 x 35 mL). All ether layer extracts were combined and dried over anhydrous sodium sulfate, followed by evaporation of the solvent. The product 2-(2-bromophenyl)-2-propanol 19.40 g was obtained in 82% yield and 95% purity (GLC assay). Physical properties of the product: boiling point 99-100 °C (5 mmHg), d420=1.1576, nD20=1.5420; MRD measured value 46.43, calculated value 46.55. Comparison of literature data: melting point 23.7 °C, boiling point 79.2 °C (2.2 mmHg), nD20=1.5416. IR spectra characteristic absorption peaks (ν, cm-1) : 3460, 1175 (OH), 1370, 1385 [C(CH3)2], 690 (C-Cl).1H NMR spectral data (δ, ppm): 1.64s (6H, CH3), 2.46s (1H, OH), 6.9-7.7m (4H, Harom). Elemental analysis measured values (%): C 63.00, H 6.42, Cl 20.71; calculated values (%) for molecular formula C9H11ClO: C 63.35, H 6.50, Cl 20.78.