[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Br[CH:10]1[C:16](=[O:17])[CH2:15][CH2:14][N:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:12][CH2:11]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:10]2[C:16](=[O:17])[CH2:15][CH2:14][N:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:12][CH2:11]2)=[CH:4][CH:3]=160.5 g (320 mmol) 4-bromothiophenol in 300 mL chloroform are added to a solution of 84.5 g (320 mmol) ethyl 4-bromo-5-oxo-azepan-1-carboxylate and 32.4 g (320 mmol) triethylamine in 80 mL chloroform over 45 min, so that the internal temperature does not exceed 40° C. The reaction solution is stirred for 1.5 h at RT. The reaction mixture is washed twice with dilute ammonia solution and twice with water. The organic phase is dried over Na2SO4 and K2CO3 and the solvent is eliminated i.vac. The purification is carried out by repeated column chromatography on silica gel.
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