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Dimethylformamide → 4-Carbazol-9-ylmethylbenzoic acid methyl ester

HRID 403645
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HRID 403645 반응식
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].CN(C)C=O.[CH3:21][O:22][C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([CH2:30]Br)=[CH:26][CH:25]=1>O>[CH3:21][O:22][C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[CH:26][CH:25]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6854CarbazoleHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoate

생성물 1

HCID 668730724-Carbazol-9-ylmethylbenzoic acid methyl ester수율 20.5%

시약·촉매·용매 1

HCID 962Water용매

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온도
60 °C

실험 절차

Carbazole (0.80 g, 4.80 mmol) and sodium hydride (NaH) (60% in mineral oil, 0.25 g, 6.2 mmol) were added to a flask, which was charged with argon. DMF (dimethylformamide) (12 mL) was added and the mixture was stirred at 60° C. for 1 hour (h), after which 4-bromomethyl benzoic acid methyl ester (1.16 g, 4.8 mmol) was added, and the mixture was stirred at 80° C. overnight. Water was added and the product was extracted with CH2Cl2 (dichloromethane), dried (Na2SO4, sodium sulfate) and concentrated. The product was purified by column chromatography to give 310 mg of compound 28 as a white solid.

후처리

  1. additionwhich was charged with argon
  2. stirringthe mixture was stirred at 80° C. overnight
  3. extractionthe product was extracted with CH2Cl2 (dichloromethane)
  4. dry with materialdried (Na2SO4, sodium sulfate)
  5. concentrationconcentrated
  6. customThe product was purified by column chromatography

출처 및 근거

ORD 기록
ord-c36c2d67a4ed49c8a260d452a962892e
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08748451B2

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