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

HRID 1265974ノート

反応式

HRID 1265974 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f4e3c1f3c3604949bc4cae5cb2e529fc
出典データセット
uspto-grants-2003_04
特許番号
US06548448B2

反応ノート

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