Ethyl Acetate → 2-Amino-6-chlorobenzenethiol hydrogen chloride, 95%

Reaction equation

C([S:8][C:9]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:16])C1C=CC=CC=1.[Al+3].[Cl-].[Cl-].[Cl-].CCOC(C)=O>C1C=CC=CC=1>[ClH:15].[NH2:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([Cl:15])[C:9]=1[SH:8]

Participants

Procedure

To a solution of 2-benzylsulfanyl-3-chloro-phenylamine (204) in 140 mL of benzene at 0° C. was added AlCl3 (Aldrich, 23.8 g, 179 mmol) in portion. The mixture turned to purple. After stirred at ambient temperature overnight, the mixture was poured to ice and EtOAc and stirred for 20 min. The mixture was extracted 3× with EtOAc (500 mL). The organic layers were washed twice with a brine solution (400 mL), dried over Na2SO4, and concentrated under vacuum. The crude product was treated with 145 mL of 1N HCl in ether. The product (13.6 g) was collected by filtration and washed with hexanes. 1H NMR (400 MHz, DMSO) δ 7.05 (t, J=8.2 Hz, 1H), 6.70 (d, J=8.2 Hz, 1H), 6.61 (d, J=7.8 Hz, 1H).