(4-Chlorophenyl)acetic acid → (4-Chlorophenyl)acetic acid tert-butyl ester

Participants

Reaction Steps

To a solution of 4-chlorophenylacetic acid (10.0 g, 58.6 mmol) in CH2Cl2 was added 2-Cert-butyl-1,3-diisopropyl-isourea (50 g, 250 mmol) dropwise at −10° C. The mixture was stirred at room temperature overnight, then the precipitate was, removed by filtration. The filtrate was washed with 1M HCl (aq) and saturated NaCl (aq), dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel chromatography eluting with 2% EtOAc/petroleum ether to afford the title compound: 1H NMR (CD3OD, 300 MHz) δ 7.26-7.30 (m, 2H), 7.18-7.21 (m, 2H), 3.49 (s, 2H), 1.43 (s, 9H).

Provenance & Evidence