[NH2:1][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.C([O-])([O-])=O.[K+].[K+].[O-]S([O-])=O.[Na+].[Na+]>CO.CC(C)=O.C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:6]2[CH:7]=[C:8]([Br:13])[C:9]([O:11][CH3:12])=[CH:10][C:5]=2[O:4][N:3]=1
To a stirred solution of 3-amino-6-methoxy-1,2-benzisoxazole (14 g) in methanol (1 L) was added a solution of bromine (13.6 g) and methanol (200 ml) dropwise at -50° C. under N2. The mixture was allowed to warm to room temperature after the addition was complete. After 24 hours an additional 1/4 equivalent of bromine was added. TLC (10% acetone/CHCl3) showed no starting material 24 hours later. The reaction was neutralized with saturated K2CO3 solution, treated with saturated Na2SO3 solution triturated with water, filtered, and washed with water. The crude product was dried in vacuo affording 14 g of product, m.p. 226°-227° C.
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