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

HRID 384337Notes

Reaction equation

HRID 384337 reaction equation
[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]

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 165971Chromium oxideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-261e4953a9114ccbb8e8ff8699cc5e11
Source dataset
uspto-grants-2013_02
Patent number
US08367710B2

Reaction notes

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