Water → Tert-butyl 4-chloro-3-nitrobenzoate

Participants

Reaction Conditions

Reaction Steps

A solution of 4-chloro-3-nitrobenzoylchloride (8.80 g, 40 mmol) in CH2Cl2 (20 mL) was added to a solution of tert-butyl alcohol (7.6 mL, 80 mmole) and pyridine (6.6 mL, 80 mmole) at 25° C. The mixture was stirred at 25° C. for 12 h then H2O (30 mL) was added. The aqueous solution was extracted with ethyl ether (3×100 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to give a yellowish solid residue. Purification of the residue by flash column chromatography (gradient elution 0 to 15% EtOAc/hexanes) provided the title compound (8.11 g, 79%): TLC (Rf =0.50; 15% EtOAc/hexanes); 1H NMR (CDCl3) δ 8.41 (s, 1H), 8.13 (d, 1H, J=8.0), 7.63 (d, 1H, J=8.3), 1.63 (s, 9H); 13C NMR (CDCl3)δ 162.4, 147.6, 133.2, 131.6, 130.5, 126.0, 124.4, 82.6, 27.8; Anal. (C11H12N1O4Cl) C, H, N.

Provenance & Evidence