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

HRID 2076636
ノート
印刷プレビュー

反応式

HRID 2076636 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-ec77beffeffa4b98ae52f157752c9123
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07923573B2

反応ノート

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