tert-Butyl hydroperoxide → 5-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-one

HRID 384337ノート

反応式

HRID 384337 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH3:12])[CH3:11])=[CH:4][CH:3]=1.C([O:17]O)(C)(C)C>ClCCl.O.[O-2].[Cr+3].[O-2].[O-2].[Cr+3]>[Br:1][C:2]1[CH:10]=[C:9]2[C:5](=[CH:4][CH:3]=1)[C:6](=[O:17])[CH2:7][C:8]2([CH3:12])[CH3:11]

参加物

6

反応物 2

HCID 6410tert-Butyl hydroperoxideHCID 124417856-bromo-1,1-dimethyl-2,3-dihydro-1H-indene

生成物 1

HCID 124417825-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-one収率 82.3%

試薬・触媒・溶媒 3

HCID 165971Chromium oxide触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

6-Bromo-1,1-dimethyl-indan 8g (4 g, 17.8 mmol) was dissolved in 40 mL of anhydrous dichloromethane, followed by addition of chromium oxide (280 mg, 1.8 mmol) and slowly dropwise addition of tert-butyl hydroperoxide (19 mL, 190 mmol). The reaction system was sealed and stirred overnight at room temperature after the reaction solution was crimson and the generated gas was released. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was diluted with 50 mL of water and extracted with dichloromethane (100 mL×3). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the title compound 5-bromo-3,3-dimethyl-indan-1-one 19a (3.5 g, 82.3%) as a white solid.

後処理

  1. customThe reaction system was sealed
  2. extractionextracted with dichloromethane (100 mL×3)
  3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-261e4953a9114ccbb8e8ff8699cc5e11
出典データセット
uspto-grants-2013_02
特許番号
US08367710B2

反応ノート

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