[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[NH:5][CH3:6].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(O)C.CCOCC>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][N:5]([C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[CH:3]=1)[CH3:6])[CH3:22]To a solution of 3-chloro-N-methylaniline (0.50 g, 3.35 mmol) in ethanol (7 ml) were added sodium carbonate (0.53 g, 5.03 mmol) and ethyl bromoacetate (0.42 ml, 3.69 mmol). The resulting suspension was stirred at room temperature for 1 hour and was then heated at 100° C. for 15 min under microwave irradiation. The mixture was then cooled to room temperature, diluted with ether, and filtered. The filtrate was washed with 1 M aqueous hydrochloric acid, the phases separated, and the aqueous phase extracted with ether. The combined organic extracts were dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (SiO2: heptane/ethyl acetate=gradient 100:0-70:30) to yield a brown oil (0.49 g, 64%); MS (ISP): 230.3, 228.1 ([M+H]+.).
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