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Nickel chloride hexahydrate (41 g, 172.5 mmol), then sodium borohydride (19.5 g, 0.516 mmol) were added to a solution of 4-nitrophenyl phenyl sulfide Compound 161a (20 g, 86.5 mmol) in a mixture of MeOH (200 mL) and THF (75 mL) at 0° C. under nitrogen over a period of 1 hr. The mixture was stirred for 30 mins at 0° C. and the reaction was quenched slowly with aqueous 10% NH4Cl, neutralized with ammonium hydroxide and partitioned between ethyl acetate and water. The organic layer was dried (Na2SO4), then filtered and the solvent evaporated in vacuo to yield 4-phenylsulfanyl-phenylamine Compound 161b (15.08 g, 87%), as a solid. MS (ES+) m/z 202.1 (M+H+). 1H NMR (400 MHz, CDCl3) δ 7.32-7.29 (2H, m), 7.22-7.18 (2H, m), 7.13-7.09 (3H, m), 6.68-6.66 (2H, m), 3.79 (2H, br s)

1. customthe reaction was quenched slowly with aqueous 10% NH4Cl
2. custompartitioned between ethyl acetate and water
3. dry with materialThe organic layer was dried (Na2SO4)
4. filtrationfiltered
5. customthe solvent evaporated in vacuo