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

HRID 1265974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1265974
[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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 185481952-(6-(Phenyldimethylsilyl)-hexyl)-1,1,2-tribromocyclopropaneAusbeute 47,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f4e3c1f3c3604949bc4cae5cb2e529fc
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06548448B2

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