[Cl:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=2[O:4][N:3]=1.[Br:13]Br.N#N.CC(C)=O.C(Cl)(Cl)(Cl)Cl>C(O)(=O)C>[Br:13][C:10]1[C:5]2[O:4][N:3]=[C:2]([Cl:1])[C:6]=2[CH:7]=[CH:8][C:9]=1[O:11][CH3:12]To a stirred solution of 3-chloro-6-methoxy-1,2-benzisoxazole (25 g) in acetic acid (200 ml) was added a solution of bromine (32.6 g) in acetic acid (100 ml) dropwise under N2 at ambient temperature. The mixture was allowed to stir overnight. TLC (silica gel, 5% acetone/CCl4) revealed the presence of starting material. Additional bromine (11 g) in acetic acid (50 ml) was added, and the reaction mixture was allowed to stir overnight. The reaction was filtered and washed with water. The precipitate was collected and recrystallized from methanol to yield the desired compound, m.p. 134°-135° C.
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