[CH3:1][S:2]([C:5]1[CH:19]=[CH:18][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=2)=[C:7]([N+:20]([O-])=O)[CH:6]=1)(=[O:4])=[O:3].C(O)(=O)C.[H][H]>[Pd].[OH-].[Na+]>[Cl:17][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[Cl:16])[O:9][C:8]1[CH:18]=[CH:19][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][C:7]=1[NH2:20]
A slurry of 10.5 g (0.0290 mole) of 4-(4-(methylsulfonyl)-2-nitrophenoxy)-1,2-dichlorobenzene and 350 ml of glacial acetic acid was placed in a Parr bottle and 0.5 g of 5% palladium on carbon added under nitrogen. The mixture was placed on a Parr hydrogenator apparatus and the desired reduction carried out with 50 pounds per square inch (psi) of hydrogen. Two batches of equal size were run and the catalyst removed by filtration. The solvent was removed in vacuo leaving crude product which was slurried in aqueous NaOH to remove any residual acetic acid. The aqueous layer was decanted from the product which was dried, to obtain 14.4 g (74.8% yield) of product. Recrystallization from ethanol and water afforded purified 2-(3,4-dichlorophenoxy)-5-(methylsulfonyl)benzenamine, mp 119°-121° C.
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