[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].Cl.[CH3:13][NH:14][O:15][CH3:16].N1C=CC=CC=1.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([N:14]([CH3:13])[O:15][CH3:16])=[O:6]To a solution of 3-bromo-2-methyl benzoic acid (430 mg, 2.00 mmol) in anhydrous DCM, under nitrogen at ambient temperature was added N,O-dimethylhydroxylamine hydrochloride (215 mg, 2.20 mmol), pyridine (0.18 mL, 2.23 mmol) and CBr4 (662 mg, 2.00 mmol). Triphenyl phosphine (576 mg, 2.20 mmol) was added portion-wise over 10 min and the resulting mixture stirred at ambient temperature for 2.5 h. The reaction mixture then reduced under vacuum and purified by SPE (silica, 10 g cartridge) eluting with cyclohexane:EtOAc (gradient 99:1 to 4:1) to afford the title compound as a colourless oil (310 mg).
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