[NH2:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].CCN(C(C)C)C(C)C.Br[CH2:22][CH2:23][O:24][CH2:25][CH2:26][Br:27].[CH3:28][CH2:29][O:30][C:31]([CH3:33])=O>CN(C=O)C>[F:11][C:3]1[C:2]([N:1]2[CH2:33][CH2:31][O:30][CH2:29][CH2:28]2)=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O:7][CH2:22][CH2:23][O:24][CH2:25][CH2:26][Br:27])=[O:6]To a solution of 3-amino-2-fluorobenzoic acid (500 mg, 3.1 mmol) in DMF (10 mL) was added DIEA (4.5 mL) and 2-bromoethylether (5 eq) and the reaction heated to 80° C. for 18 h. The reaction was allowed to cool to rt, diluted with EtOAc and washed with saturated NH4Cl (aq). The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was purified by column chromatography (petroleum ether: EtOAc) to give 2-(2-bromoethoxy)ethyl 2-fluoro-3-morpholinobenzoate (450 mg, 38%) as a yellow oil.
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