[NH2:1][C:2]1[C:10]2[O:9][C:8]([CH3:12])([CH3:11])[O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[F:13].[Cl:14]N1C(=O)CCC1=O.C(Cl)Cl.CCCCCCC>CN(C)C=O>[NH2:1][C:2]1[C:10]2[O:9][C:8]([CH3:11])([CH3:12])[O:7][C:6]=2[C:5]([Cl:14])=[CH:4][C:3]=1[F:13]In a flask were placed 2.23 g (0.0122 mole) of 4-amino-2,2-dimethyl-5-fluoro-1,3-benzodioxole and 40 mL of N,N-dimethylformamide. To this solution was added in a dropwise manner a solution of 1.79 g (0.0134 mole) of N-chlorosuccinimide in N,N-dimethylformamide while maintaining the temperature at ambient conditions. The solvent was evaporated under reduced pressure, leaving a residue which was passed through a column of silica gel eluting with methylene chloride/heptane (1:1 ). Product-containing fractions were combined and the solvent evaporated, yielding 1.93 g of 4-amino-7-chloro-2,2-dimethyl-5-fluoro-1,3-benzodioxole as the residue. The NMR spectrum was consistent with the proposed structure.
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