Water → 2-Bromo-3-(2-methoxyphenyl)-3-oxo-propionic acid ethyl ester

Reaction equation

[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15])=[O:7])[CH3:2].[Br:17]N1C(=O)CCC1=O.O>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([Br:17])[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15])=[O:7])[CH3:2]

Participants

Procedure

To a solution of 3-(2-methoxy-phenyl)-3-oxo-propionic acid ethyl ester (5.3 g, 23.9 mmol; prepared as reported in J. Org. Chem. 2001, 66, 6323-6332) in carbon tetrachloride (50 ml) was added of N-bromosuccinimide (5.1 g, 28.7 mmol) portion-wise The reaction mixture was stirred at room temperature under an Ar atmosphere for 4 hours. Water was added, the resulting mixture was extracted with CHCl3, and the organics were dried over Na2SO4 and evaporated under reduced pressure to yield the title compound as a yellow oil. 1H NMR (200 MHz, CDCl3) δ 1.25 (t, 3H, COOCH2CH3, J=7), 3.92 (s, 3H, OCH3), 4.25 (q, 2H, COOCH2CH3, J=6.4), 5.82 (s, 1H, CHBr), 6.97-7.11 (m, 2H, Ar), 7.51-7.60 (m, 1H, Ar), 7.90-7.95 (m, 1H, Ar).