Bromoform → (2,2-Dibromo-1-methylcyclopropyl)benzene

HRID 1265979Notes

Reaction equation

HRID 1265979 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].[CH:10]([Br:13])(Br)[Br:11].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:11][C:10]1([Br:13])[CH2:1][C:2]1([CH3:3])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 5558BromoformHCID 7407Alpha-MethylstyreneHCID 14798Sodium Hydroxide2×

Product 1

HCID 308177(2,2-Dibromo-1-methylcyclopropyl)benzeneYield 86.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

To a solution of 12.5 ml (0.0963 mol) of α-methylstyrene in 30.4 ml (0.348 mol) of bromoform and 1.34 g (0.00416 mol) of tetrabutylammonium bromide was added slowly via addition funnel 20.9 ml (0.400 mol) of 50% aqueous sodium hydroxide. After heating to 55° C. for 1 hour 20.9 ml (0.400 mol) of 50% aqueous sodium hydroxide was added. After 2 additional hours of heating, the reaction was cooled to room temperature when hexanes and water were added. The resulting mixture was transferred to a separatory funnel and the phases were separated. The organic layer was dried over MgSO4 and filtered. The solvent was removed from the filtrate in vacuo. The product was isolated by vacuum distillation to yield 24.1 g of 2,2-dibromo-1-methyl-1-phenylcyclopropane as an oil.

Workup

  1. additionwas added
  2. temperatureAfter 2 additional hours of heating
  3. additionwere added
  4. customThe resulting mixture was transferred to a separatory funnel
  5. customthe phases were separated
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed from the filtrate in vacuo
  9. customThe product was isolated by vacuum distillation

Sources & evidence

ORD record
ord-ce91426ac9804427a835626f6cf6bebb
Source dataset
uspto-grants-2003_04
Patent number
US06548448B2

Reaction notes

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