Methyl 4-(4-chloro-2-methylbutan-2-ylthio)-3-nitrobenzoate → Methyl 3-amino-4-(4-chloro-2-methylbutan-2-ylthio)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-(4-chloro-2-methylbutan-2-ylthio)-3-nitrobenzoate (3.43 g, 10.8 mmol) in AcOH (100 mL) was added iron (2.413 g, 43.2 mmol). The reaction was heated to 70° C. and stirred at that temperature for 2 hours. The solvent was removed under reduced pressure and the resulting paste was diluted with H2O (250 mL). The solution was treated with K3PO4 until pH=6. The aqueous layer was extracted with EtOAc (3×150 mL). The combined organics were washed with saturated aqueous NaHCO3 (50 mL) and brine (50 mL) then dried over Na2SO4 and concentrated in vacuo. The product was isolated as a brown solid and used without further purification.

Provenance & Evidence