tert-Butyl acrylate → 3-(3,5-Dichloro-phenyl)-acrylic acid tert butyl ester

Beteiligte Stoffe

Reaktionsschritte

A mixture of 3,5-dichloro-iodobenzene (5 g, 18 mmol), tert butyl acrylate (6.5 mL, 2.5 eq), tetrabutyl ammonium chloride hydrate (5.1 g, 1 eq), potassium acetate (5.4 g, 3 eq) and palladium (II) acetate (˜200 mg, 30 mol %) in DMF (50 mL) was stirred at ambient temperature for 5 h. The reaction mixture was reduced in vacuo and partitioned between water and ethyl acetate. The ethyl acetate fractions were dried over magnesium sulphate and filtered through a small plug of silica gel using 10% ethyl aceate/n-heptanes as eluent to afford 3-(3,5-dichlorophenyl)-acrylic acid tert butyl ester as a white solid. 1H-NMR (DMSO-d6, 400 MHz): δ 7.81 (d, J=1.77 Hz, 2H), 7.59 (t, J=1.89 Hz, 1H), 7.49 (d, J=16.04 Hz, 1H), 6.69 (d, J=16.04 Hz, 1H), 1.46 (s, 9H).

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