[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([OH:14])=O.Cl.[CH3:16][NH:17][O:18][CH3:19].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([N:17]([O:18][CH3:19])[CH3:16])=[O:14]To a mixture of 1-bromo-2-naphthoic acid (1.04 g, 4.14 mmol, TCI America) and N,O-dimethylhydroxylamine hydrochloride (0.465 g, 4.76 mmol) in N,N-dimethylformamide (10 mL,) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (2.11 g, 4.76 mmol). After stirred at room temperature for 10 minutes, N,N-diisopropylethylamine (2.16 mL, 12.4 mmol) was added to the resulting mixture. The reaction was stirred at room temperature for 2 h, quenched with water, and extracted with EtOAc. The combined organic layers were washed with water, brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was concentrated and the residue was purified on silica gel, eluting with 0% to 50% ethyl acetate in hexane, to give the desired product (1.08 g, 88%). LCMS calculated for C13H13BrNO2(M+H)+: m/z=294.0; found: 294.2.
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