[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.Cl.[NH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:3]=1A solution of 4-bromo-2-fluoro-1-nitrobenzene (10 g, 45.5 mol), methyl 3-aminopropanoate hydrochloride (6.4 g, 45.5 mol) and K2CO3 (19 g, 136.5 mol) in THF (250 mL) was heated at 100° C. for 4 hrs. The mixture was extracted with ethyl acetate (100 mL), washed with brine (150 mL), dried and concentrated to give the residue, which was purified by CombiFlash (PE:EA=2:1) to give methyl 3-((5-bromo-2-nitrophenyl)amino)propanoate (12 g, yield 88%). 1H NMR (300 MHz, CDCl3) δ 2.70-2.75 (t, J=6.6 Hz, 2H), 3.58-3.65 (m, 2H), 3.74 (s, 3H), 6.76-6.80 (m, 1H), 7.02-7.03 (d, J=2.1 Hz, 1H), 8.01-8.04 (d, J=9.0 Hz, 2H), 8.20-8.22 (br, 1H).
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