Bromoform → 1,1,2-Tribromo-2-hexyl-cyclopropane

HRID 840060Notes

Reaction equation

HRID 840060 reaction equation
[Br:1][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[CH2:3].[CH:10]([Br:13])(Br)[Br:11].[Br-].[Br-].C([N+](C)(C)CC[N+](CC1C=CC=CC=1)(C)C)C1C=CC=CC=1.[OH-].[K+]>C(Cl)Cl.O>[Br:11][C:10]1([Br:13])[CH2:3][C:2]1([Br:1])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

7

Reactant 4

HCID 5558BromoformHCID 14797Potassium HydroxideHCID 123896162-Bromo-1-octeneHCID 22146564N,N'-dibenzyl-N,N,N',N'-tetramethylethylenediammonium dibromide

Product 1

HCID 226216761,1,2-Tribromo-2-hexyl-cyclopropaneYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To 5.42 g (0.0284 mol) of 2-bromo-oct-1-ene in 7.42 ml (0.0851 mol) of bromoform and 48.8 ml of methylene chloride, were added 1.30 g ( 0.00284 mol) of N,N′-dibenzyl-N,N,N′,N′-tetramethylethylenediammonium dibromide and 12.1 ml (0.142 mol) of 45% aqueous potassium hydroxide. The mixture was left at room temperature for 5 days. There was then added hexanes and water. This mixture was gravity filtered through qualitative fluted filter paper. 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 to yield 5.25 g (51.0% of theoretical) of 1,1,2-tribromo-2-hexyl-cyclopropane as an oil.

Workup

  1. filtrationfiltered through qualitative fluted filter paper
  2. customThe resulting mixture was transferred to a separatory funnel
  3. customthe phases were separated
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed from the filtrate in vacuo

Sources & evidence

ORD record
ord-aba013ec0ec546b9b19a6db02455c503
Source dataset
uspto-grants-2002_04
Patent number
US06365549B2

Reaction notes

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