3-Bromobenzonitrile → Tert-butyl 2-(3-cyanophenyl)acetate

Participants

Reaction Steps

Combined 3-bromobenzonitrile (1500 mg, 8.24 mmol), 0.5 M (2-(tert-butoxy)-2-oxoethyl)zinc(II) chloride (24.72 mL, 12.36 mmol), 2′-(dicyclohexylphosphino)-N,N-dimethyl-[1,1′-biphenyl]-2-amine (324 mg, 0.824 mmol) and Pd(dba)2 (237 mg, 0.412 mmol) in THF (25 mL) and heated at 100° in an oil bath for 14 h. The reaction solution was concentrated onto Celite® and chromatographed on a 120 g silica gel column eluted with 0 to 50% EtOAc in hexanes to give the title compound (1.537 g, 86% yield) as a yellow oil. MS m/z 218 [M+H]+. 1H NMR (400 MHz, chloroform-d) δ ppm 1.45 (s, 9 H) 3.56 (s, 2 H) 7.40-7.46 (m, 1 H) 7.49-7.54 (m, 1 H) 7.54-7.59 (m, 2 H).

Provenance & Evidence