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

HRID 2195098ノート

反応式

HRID 2195098 の反応式
[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

参加物

7

反応物 4

HCID 24479Stannous ChlorideHCID 288478(Benzo(1,2-b:4,5-b)dithiophene-4,8-dione)HCID 27356021-Bromo-10-phenyldecaneHCID 5462224Magnesium2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1faaf38a02fa4bee8402e797952b8541
出典データセット
uspto-grants-2012_12
特許番号
US08334456B2

反応ノート

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