Acetic Acid → Ethyl 2-(4-bromo-2-nitrophenyl)acetate
Reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17])C(OC)=O.Cl.[C:21](O)(=O)C>>[CH2:1]([O:2][C:3](=[O:19])[CH2:4][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17])[CH3:21]Participants
4
Conditions
- Temperature
- 110 °C
Procedure
To a suspension of 2-(4-bromo-2-nitro-phenyl)-malonic acid dimethyl ester (crude, 8.1 mmol) in acetic acid (10 mL) is added 6N HCl (10 mL). The mixture is heated at 110° C. overnight (about 15 hr). The reaction mixture is evaporated to dryness. The crude is used in the next step without further purification. To a solution of the crude in ethanol (40 mL) is added concentrated H2SO4 (3 drops) and the resulting reaction mixture is heated at reflux over night. Solvent is removed under reduced pressure. It is purified by flash column chromatography. 1H NMR (400 MHz, CDCl3) δ 8.25 (s, 1 H), 7.72-7.7 (m, 1 H), 7.26-7.22 (m, 1 H), 4.23-4.13 (q, 2 H), 3.97 (s, 2 H), 1.29-1.23 (t, 3 H).