Isobutyryl chloride → Ethyl 4-isobutyrylbenzoate

Participants

Reaction Conditions

Reaction Steps

To a 100-mL round-bottom flask was added THF (25 mL). The solvent was bubbled with nitrogen for a few minutes then cooled to 0° C. and added bis(triphenylphosphine)palladium(II) chloride (0.44 g, 0.63 mmol) followed by 4-(ethoxycarbonyl)phenylzinciodide (25.0 mL, 12.5 mmol; 0.50 M in THF). After stirred at at 0° C. for 15 min, isobutyryl chloride (1.32 mL, 12.5 mmol) was added and the resulting mixture was stirred at 0° C. for 2 h. The reaction was quenched with slow addition of 1 N HCl and extracted with EtOAc (3×100 mL). After separation, combined organic extracts were washed with sat. NaHCO3, water, brine, dried (MgSO4), and concentrated. Flash column chromatography (EtOAc:hexanes, 0:1 to 1:9) afforded ethyl 4-isobutyrylbenzoate (2.49 g, 90%) as a slight-brown oil. LC-MS: (FA) ES+ 221; 1H NMR (CDCl3, 400 MHz) δ8.13 (d, J=8.5 Hz, 2H), 7.99 (d, J=8.5 Hz, 2H), 4.40 (q, J=7.2 Hz, 2H), 3.56 (m, 1H), 1.42 (t, J=7.2 Hz, 3H), 1.23 (d, J=7.2 Hz, 6H).

Provenance & Evidence