Dichloromethane → HCID 21881427, compound

HRID 1442467Notes

Reaction equation

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]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To 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.

Workup

temperatureThe reaction mixture was cooled
washThe organic layer was further washed with 1N HCl and water (twice),
dry with materialdried by MgSO4
customthe solvent was removed in vacao
customThe crude product was further purified by column chromatography (hexane/dichloromethane 6/1)

Sources & evidence

ORD record: ord-749285f130b84bdd96a99c09ef566f0c
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07658868B2

Reaction notes

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