Stannous Chloride → 4,8-Bis(10-phenyldecyl)benzo[1,2-b:4,5-b']dithiophene

HRID 2195098노트

반응식

HRID 2195098 반응식
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[S:19]1[CH:23]=[CH:22][C:21]2[C:24](=O)[C:25]3[S:26][CH:27]=[CH:28][C:29]=3[C:30](=O)[C:20]1=2.Cl[Sn]Cl>C1COCC1.[Cl-].[Na+].O>[C:13]1([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:24]2[C:25]3[S:26][CH:27]=[CH:28][C:29]=3[C:30]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:20]3[S:19][CH:23]=[CH:22][C:21]=23)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

7

반응물 4

HCID 24479Stannous ChlorideHCID 288478(Benzo(1,2-b:4,5-b)dithiophene-4,8-dione)HCID 27356021-Bromo-10-phenyldecaneHCID 5462224Magnesium2회

생성물 1

HCID 668211144,8-Bis(10-phenyldecyl)benzo[1,2-b:4,5-b']dithiophene수율 15%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 57417360Sodium chloride; water용매

실험 절차

To a 100 mL flask under nitrogen was added magnesium (486 mg, 20 mmol) and anhydrous THF (10 mL). The mixture was heated under reflux and 10-bromodecylbenzene (5.95 g, 20 mmol) was added dropwise. The reaction mixture was kept under reflex temperatures until all magnesium was consumed. Subsequently, 4,8-dihydrobenzo[1,2-b:4,5-b′]dithiophene-4,8-dione (1.1 g, 5.0 mmol) suspended in anhydrous THF (10 ml) was added dropwise. After refluxing for 3 hours more, it was cooled down to room temperature. SnCl2 solution (7.5 g in 19 mL 10% HCl) was slowly added dropwise and then the mixture was kept at 60° C. overnight. After cooling down, brine (25 mL) was added. The organic phase was separated and dried over Na2SO4. The residue after vacuum evaporation was purified by column chromatography with hexane/AcOEt 50:1 as eluent and gave a pale yellow oil (466 mg, yield 15%), which turned into a solid upon standing for a few days. 1H NMR (CDCl3, 500 MHz) δ=7.48 (d, J=6.0 Hz, 2H), 7.46 (d, J=5.0 Hz, 2H), 7.27-7.32 (m, 4H), 7.19 (d, J=7.0 Hz, 6H), 3.19 (t, J=8.0 Hz, 4H), 2.61 (t, J=7.5 Hz, 4H), 1.75-1.86 (m, 4H), 1.58-1.67 (m, 4H), 1.42-1.51 (m, 4H), 1.15-1.41 (m, 20H).

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. customwas consumed
  4. additionwas added dropwise
  5. temperatureAfter refluxing for 3 hours more
  6. temperatureAfter cooling down
  7. customThe organic phase was separated
  8. dry with materialdried over Na2SO4
  9. customThe residue after vacuum evaporation
  10. customwas purified by column chromatography with hexane/AcOEt 50:1 as eluent

출처 및 근거

ORD 기록
ord-1faaf38a02fa4bee8402e797952b8541
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334456B2

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