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

HRID 384337노트

반응식

HRID 384337 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 165971Chromium oxide촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-261e4953a9114ccbb8e8ff8699cc5e11
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367710B2

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