[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:16][O:17][CH2:18][CH2:19]Br.[I-].[Na+].C(=O)(O)[O-].[Na+].FC(F)(F)C(O)=O>O.CCOCC.C(OCC)(=O)C.CC#N.O.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:19][CH2:18][O:17][CH3:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]
Ethyl N-(3,4-dichlorophenyl)glycinate (3.0 g, 12.1 mmol) was suspended in 2-bromoethyl methyl ether (9.09 mL, 96.7 mmol) and treated with sodium iodide (1.81 g, 12.1 mmol), sodium bicarbonate (1.02 g, 12.1 mmol), and 10 mL of DMF. The reaction was stirred for 20 hours at room temperature, but HPLC (Eclipse XDB-C18, 4.6×250 mm, 5 micron, 1-99% CH3CN/H2O with 0.1% trifluoroacetic acid) indicated that only starting material (Rt=8.0 min) was present and that no reaction had taken place. The reaction was heated to 125° C. for 24 hours, after which time HPLC showed that all of the starting material was gone and that a new product peak had formed (Rt=8.7 min). The reaction mixture was poured into 200 mL of ethyl acetate, 100 mL of ether, and 250 mL of water and shaken vigorously. The layers were separated and the organic layer was washed with water (1×400 mL), dried over magnesium sulfate, filtered, and concentrated to a black oil. The oil was adsorbed onto approximately 50 g of silica gel and purified by column chromatography (300 g silica gel 40 um, gradient elution from 10% ethyl acetate/90% hexanes to 100% ethyl acetate over 110 minutes) to give ethyl N-(3,4-dichlorophenyl)-N-[2-(methyloxy)ethyl]glycinate (0.73 g, 2.39 mmol, 20%) as a brown oil. MS (ES) m/e 306 [M+H]+.
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