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

HRID 1265974노트

반응식

HRID 1265974 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f4e3c1f3c3604949bc4cae5cb2e529fc
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06548448B2

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