Potassium Hydroxide → 2,7-Dichloro-9-(3,7-dimethyl-octyl)-9H-carbazole

HRID 722676

반응식

HRID 722676 반응식
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Cl:15])=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.[OH-].[K+].CCCCCCCC(C([NH3+])(C(CCCCCCC)=O)C(CCCCCCC)=O)=O.[Cl-].Br[CH2:49][CH2:50][CH:51]([CH3:58])[CH2:52][CH2:53][CH2:54][CH:55]([CH3:57])[CH3:56]>C(Cl)Cl>[Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Cl:15])=[CH:9][CH:10]=3)[N:5]([CH2:49][CH2:50][CH:51]([CH3:58])[CH2:52][CH2:53][CH2:54][CH:55]([CH3:57])[CH3:56])[C:4]=2[CH:3]=1

참가 물질

6

반응물 4

HCID 14797Potassium HydroxideHCID 1379141-Bromo-3,7-dimethyloctaneHCID 12070509Carbazole, 2,7-dichloro-HCID 77620884Tricaprylylmethyl ammonium chloride

생성물 1

HCID 218856252,7-Dichloro-9-(3,7-dimethyl-octyl)-9H-carbazole

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
85 °C

실험 절차

2,7-Dichlorocarbazole (synthesized according to the procedure by Leclerc et al: Morin, Jean-Francois; Leclerc, Mario; Macromolecules (2001), 34(14), 4680–4682) (10.7 g, 45.3 mmol) was added to a 50% w/w aqueous solution of potassium hydroxide (75 ml) and Aliquat-336 (0.5 ml). 1-Bromo-3,7-dimethyloctane (12.0 g, 54.3 mmol) was added dropwise and the reaction mixture was heated at 85° C. for 12 h. After cooling to room temperature, methylene chloride was added. The reaction mixture was transferred to a separation funnel and the organic layer was removed. The aqueous layer was extracted with methylene chloride (3×) and the combined organic layers were dried over magnesium sulfate. After removal of the solvent in vacuo, the crude product was purified by column chromatography (silica gel, hexane) to yield 13.5 g of the product as colorless solid.

후처리

  1. temperatureAfter cooling to room temperature
  2. customThe reaction mixture was transferred to a separation funnel
  3. customthe organic layer was removed
  4. extractionThe aqueous layer was extracted with methylene chloride (3×)
  5. dry with materialthe combined organic layers were dried over magnesium sulfate
  6. customAfter removal of the solvent in vacuo
  7. customthe crude product was purified by column chromatography (silica gel, hexane)

출처 및 근거

ORD 기록
ord-0712d418553b47908225e48228690562
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138483B2

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