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Benzoyl Peroxide → Tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoate

HRID 2076636
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HRID 2076636 반응식
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:27]([O:31][C:32]([O:34][C:35]1[C:47]([C:48]([F:51])([F:50])[F:49])=[CH:46][CH:45]=[C:44]([CH3:52])[C:36]=1[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:33])([CH3:30])([CH3:29])[CH3:28]>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:52][C:44]1[C:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[C:35]([O:34][C:32]([O:31][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:33])[C:47]([C:48]([F:49])([F:50])[F:51])=[CH:46][CH:45]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 67119250Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-methyl-3-(trifluoromethyl)benzoate

생성물 1

HCID 67119234Tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoate수율 52%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride
용매

실험 절차

N-Bromosuccinimide (9.70 g, 54.5 mmol) and benzoyl peroxide (0.7 g) were added to a solution of tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-methyl-3-(trifluoromethyl)benzoate (18.6 g, 49.6 mmol) obtained in Example (28-4) in carbon tetrachloride (400 ml), and the mixture was heated under reflux for 5 hours. The temperature of the reaction mixture was returned to room temperature and the solvent was removed under reduced pressure. After n-hexane was added to the obtained residue and the mixture was filtered, the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluting solvent: toluene) to give tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoate (11.66 g, yield: 52%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customwas returned to room temperature
  4. customthe solvent was removed under reduced pressure
  5. additionAfter n-hexane was added to the obtained residue
  6. filtrationthe mixture was filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (eluting solvent: toluene)

출처 및 근거

ORD 기록
ord-ec77beffeffa4b98ae52f157752c9123
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07923573B2

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