Ethanol → Ethyl 2-(2-chloro-4-fluoro-5-nitrophenyl)acetate

Participants

Reaction Steps

A solution of 2-(2-chloro-4-fluoro-5-nitrophenyl)acetic acid (20.5 g, 88 mmol) in ethanol (150 mL) was treated with sulfuryl dichloride (21 g, 0.17 mol) at 0° C., then the mixture was heated to reflux for 1 h. The reaction mixture was concentrated under reduced pressure and the pH was adjusted to between pH 7-8 by addition of saturated Na2CO3 solution. Then resultant mixture was extracted with EtOAc (3×100 mL) and the combined organic layers were washed with brine, dried (MgSO4) and concentrated to give ethyl 2-(2-chloro-4-fluoro-5-nitrophenyl)acetate (22.5 g, 97.8%). 1HNMR (400 Hz, DMSO-d6): δ 8.32 (d, J=8.0 Hz, 1 H), 7.91 (d, J=11.2 Hz, 1 H), 4.09 (q, J=7.2 Hz, 2 H), 3.92 (s, 2 H), 1.17 (t, J=7.2 Hz, 3 H).

Provenance & Evidence