1-Bromo-2-Chloroethane → 2-(2-Chloroethylthio)aniline
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[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[OH-].[Na+].Br[CH2:12][CH2:13][Cl:14]>C(O)C.O.C(OCC)(=O)C>[Cl:14][CH2:13][CH2:12][S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH2:1][NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[OH-].[Na+].Br[CH2:12][CH2:13][Cl:14]>C(O)C.O.C(OCC)(=O)C>[Cl:14][CH2:13][CH2:12][S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH2:1]To a stirred solution of 2-aminobenzenethiol (0.513 mL, 4.79 mmol) in ethanol (5 mL) was added sodium hydroxide (192 mg, 4.79 mmol) as a solution in water (5.00 mL). To the resulting mixture was added 1-bromo-2-chloroethane (1.197 mL, 14.38 mmol), and the resulting mixture was stirred vigorously for 20 minutes The mixture was then diluted with ethyl acetate and washed with saturated sodium carbonate (3×). The organic phase was dried, filtered, and concentrated, giving a yellow liquid, 2-(2-chloroethylthio)aniline (875 mg, 97%). 1H NMR (DMSO-d6) δ 7.27 (d, J=7.5 Hz, 1H), 7.10-7.04 (m, 1H), 6.73 (d, J=8.1 Hz, 1H), 6.56-6.49 (m, 1H), 5.41 (brs, 2H), 3.62 (t, J=7.4 Hz, 2H), 3.02 (t, J=7.4 Hz, 2H). ESI-MS (m/z, %): 188 (MH+, 100).
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