3-Bromotoluene → Ethyl (4-bromo-2-methylphenyl)(oxo)acetate

Participants

Reaction Steps

To a suspension of AlCl3 (20.3 g, 152 mmol) in dichloroethane (250 mL, DCE) was added ethyl chlorooxoacetate (16.8 g, 123 mmol) at room temperature. To the resulting gold solution was added 3-bromotoluene (20.0 g, 117 mmol) and the dark solution was stirred at room temperature for 4 h. The reaction was cooled to 0° C. and saturated aqueous ammonium chloride was slowly added. The phases were separated and the DCE layer was washed with additional ammonium chloride, dried (Na2SO4), filtered, and the DCE removed in vacuo to give the crude product as a gold oil. Flash chromatography (SiO2; 0-3% Et2O/Hexanes) gave ethyl (4-bromo-2-methylphenyl)-(oxo)acetate (16.2 g; 33%) as a gold oil. 1H NMR (CDCl3) δ 1.41 (t, 3H, J=7.0 Hz), 2.58 (s, 3H), 4.43 (q, 2H, J=7.0 Hz), 7.44-7.48 (m, 2H), 7.58 (d, 1H, J=8.0 Hz); EI/MS 271 m/e (M+). Ethyl (4-bromo-2-methylphenyl)-(methoxyimino)ethanoate

Provenance & Evidence