1,2-Dibromoethane → 1-(3-Bromophenyl)cyclopropane-1-carbonitrile

HRID 216620

反応式

HRID 216620 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.Br[CH2:12][CH2:13]Br>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:9]#[N:10])[CH2:13][CH2:12]2)[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 78391,2-DibromoethaneHCID 36023(3-Bromophenyl)acetonitrile

生成物 1

HCID 200261781-(3-Bromophenyl)cyclopropane-1-carbonitrile収率 95%

試薬・触媒・溶媒 2

HCID 66133Benzyl triethylammonium chloride触媒HCID 14798Sodium Hydroxide溶媒

実験手順

3-Bromophenylacetonitrile (5.0 g, 26 mmol) and 1,2-dibromoethane (6.6 mL, 77 mmol) were added to a solution of benzyltriethylammonium chloride (0.30 g, 1.3 mmol) in 50% sodium hydroxide aqueous solution (20 mL), and the mixture was stirred at room temperature overnight. Ice-water (70 mL) was added to the reaction mixture, and the whole was extracted with ethyl acetate (50 mL). The organic layer was washed with brine (30 mL), and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography to give the title reference compound (5.4 q) as brown oil (yield 95%).

後処理

  1. extractionthe whole was extracted with ethyl acetate (50 mL)
  2. washThe organic layer was washed with brine (30 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter the solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-15fd5f118daf44cca02e80d71baab603
出典データセット
uspto-grants-2012_06
特許番号
US08193237B2

関連ノート

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