Ethanol → Ethyl 2-(2-chloro-5-nitrophenyl)acetate

Participants

Reaction Steps

Thionyl chloride (16.7 g, 0.14 mol) was added dropwise to a 0° C. solution of (2-chloro-5-nitro-phenyl)acetic acid (15 g, 0.07 mol) in EtOH (300 mL) and the resultant mixture was heated at reflux overnight. The reaction mixture was concentrated under reduced pressure and the residue was poured into ice water, and extracted with EtOAc (2×300 mL). The combined organics were washed with brine and saturated NaHCO3 solution, were dried over Na2SO4, and were concentrated in vacuo to give ethyl 2-(2-chloro-5-nitrophenyl)acetate (17 g, 99% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.35 (d, J= 2.8 Hz, 1 H), 8.12 (dd, J=8.4, 2.8 Hz, 1 H), 7.72 (d, J=8.4 Hz, 1 H), 4.10 (q, J=7.2 Hz, 2 H), 3.96 (s, 2 H), 1.15 (t, J=7.2 Hz, 3 H).

Provenance & Evidence