Bromoform → 2-(6-(Phenyldimethylsilyl)-hexyl)-1,1,2-tribromocyclopropane

HRID 1265974Notes

Reaction equation

HRID 1265974 reaction equation
[Br:1][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][Si:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:12])[CH3:11])=[CH2:3].[OH-].[K+].[Br-].[Br-].C([N+](CC)(CC)CC[N+](CC1C=CC=CC=1)(CC)CC)C1C=CC=CC=1.[CH:49]([Br:52])(Br)[Br:50]>C(Cl)Cl.O>[C:13]1([Si:10]([CH3:12])([CH3:11])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:2]2([Br:1])[CH2:3][C:49]2([Br:52])[Br:50])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 5558BromoformHCID 14797Potassium HydroxideHCID 185482212-Bromo-8-(phenyldimethylsilyl)-oct-1-eneHCID 22146562N,N'-dibenzyl-N,N,N',N'-tetraethylethylenediammonium dibromide

Product 1

HCID 185481952-(6-(Phenyldimethylsilyl)-hexyl)-1,1,2-tribromocyclopropaneYield 47.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1.4 g (4.3 mmol) of 2-bromo-8-(phenyldimethylsilyl)-oct-1-ene, 3.2 g of 45% aqueous potassium hydroxide solution (25.6 mmol), 0.2 g N,N′-dibenzyl-N,N,N′,N′-tetraethylethylenediammonium dibromide, and 7.5 ml of methylene chloride was treated with 1.1 ml of bromoform (12.6 mmol). The well-stirred reaction mixture was held overnight at room temperature. Water and methylene chloride were added, the phases were separated. The methylene chloride phase was dried over magnesium sulfate, and stripped. A small amount of heptane was added during the strip to help remove remaining bromoform. Column chromatography gave 1.02 g of 2-(6-(phenyldimethylsilyl)-hexyl)-1,1,2-tribromocyclopropane as a colorless liquid.

Workup

  1. customThe well-stirred reaction mixture
  2. customthe phases were separated
  3. dry with materialThe methylene chloride phase was dried over magnesium sulfate
  4. additionA small amount of heptane was added during the strip
  5. customto help remove

Sources & evidence

ORD record
ord-f4e3c1f3c3604949bc4cae5cb2e529fc
Source dataset
uspto-grants-2003_04
Patent number
US06548448B2

Reaction notes

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