C(N(CC)CC)C.[C:8]1([SH:15])[C:9]([SH:14])=[CH:10][CH:11]=[CH:12][CH:13]=1.F[C:17]1[CH:22]=[C:21]([Br:23])[C:20]([Br:24])=[CH:19][C:18]=1F.ClCCl>CN(C=O)C>[Br:24][C:20]1[C:21]([Br:23])=[CH:22][C:17]2[S:15][C:8]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[S:14][C:18]=2[CH:19]=1To a solution of triethylamine (0.1 mL) in 10 mL DMF, 1,2-benzenedithiol (272 mg, 1 mmole) in 1 mL DMF and 1,2-difluoro-4,5-dibromobenzene (171 mg, 1.2 mmole) in 1 mL DMF was slowly added separately at the same time with continued stirring and under Ar. The reaction mixture was heated at 80° C. for over night. The solution was then turned dark yellow. The reaction mixture was cooled and poured into dichloromethane (50 mL). The organic layer was further washed with 1N HCl and water (twice), dried by MgSO4, and the solvent was removed in vacao. The crude product was further purified by column chromatography (hexane/dichloromethane 6/1) to yield white solids (217 mg, 58%). mp 160˜161° C. 1H NMR (300 MHz, CDCl3) δ: 7.67 (s, 2H), 7.40 (dd (AA′XX′), 2H, JAX=5.7 Hz and JAX′=3.3 Hz), 7.24 (dd (AA′XX′), 2H, JAX=3.3 Hz and JAX′=2.7 Hz). 13C NMR (75 MHz, CDCl3) δ: 136.4, 134.4, 132.3, 128.8, 128.0, 123.6. FT-IR (KBr)v/cm−1: 3059, 1451, 1429, 1304, 1106, 1056, 879, 826, 746, 662, 576, 473, 441. HR-MS (EI): calcd. for Cl2H6Br2S2 371.8272 [M+]. Found 371.8283.
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