4.6. Methyl-2-(3-bromophenyl)acetate (9)

JE Janna Ehlert
JK Jenny Kronemann
NZ Nadine Zumbrägel
MP Matthias Preller
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3-Bromo phenyl acetic acid (8, 4 g, 18.7 mmol, 1.0 eq) and dried K2CO3 (8.84 g, 56 mmol, 3.0 eq) were dissolved in acetone (40 mL) under inert conditions. Methyl iodide (10.5 mL, 56 mmol, 3.0 eq) was added dropwise and the reaction mixture was stirred for 67 h at 30 °C. After cooling the reaction to room temperature, the suspension was filtered with Celite and the solvent was removed in vacuo. The crude product was purified by silica gel chromatography (PE:EtOAc/4:1) yielding the product methyl-2-(3-bromophenyl)acetate (9) after evaporation as colorless oil in 100% yield (4.25 g, 18.7 mmol, quant.). Rf (PE:EtOAc/3:1): 0.85; 1H-NMR (400 MHz, CD3Cl): δ = 7.44 (d, J = 1.5 Hz, 1H), 7.41 (dt, J = 6.5, 2.2 Hz, 1H), 7.23–7.17 (m, 2H), 3.71 (s, 3H), 3.60 ppm (s, 2H); 13C-NMR (100 MHz, CD3Cl): δ (ppm) = 171.4, 136.1, 132.4, 130.3, 130.1, 128.0, 122.6, 52.2, 40.7.

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