1,2-Dibromoethane → 1-[p-(2-Thenoyl)phenyl]cyclopropanecarbonitrile

HRID 461749Notes

Reaction equation

HRID 461749 reaction equation
[C:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[N:16])=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:18][CH2:19]Br.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[C:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3([C:15]#[N:16])[CH2:19][CH2:18]3)=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 122329742-[p-(2-Thenoyl)phenyl]acetonitrile

Product 1

HCID 122329781-[p-(2-Thenoyl)phenyl]cyclopropanecarbonitrile

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Conditions

Temperature
50 °C

Procedure

To a stirred mixture of 26 parts of 2-[p-(2-thenoyl)phenyl]acetonitrile, 34 parts of 1,2-dibromoethane and 1.6 parts of benzyl triethyl ammonium chloride are added dropwise 60 parts of sodium hydroxide solution 20N (exothermic reaction: temperature rises to 50° C - cooling is necessary to keep the temperature at 50° C). Upon completion, stirring at 50° C is continued for 4 hours. The product is extracted with toluene. The organic layer is separated, washed three times with water, dried, filtered and evaporated. The solid residue is crystallized from acetonitrile, yielding 12.2 parts of 1-[p-(2-thenoyl)phenyl]cyclopropanecarbonitrile; m.p. 105.8° C.

Workup

  1. customexothermic reaction
  2. customrises to 50° C
  3. temperaturecooling
  4. customat 50° C
  5. extractionThe product is extracted with toluene
  6. customThe organic layer is separated
  7. washwashed three times with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customThe solid residue is crystallized from acetonitrile

Sources & evidence

ORD record
ord-394cd9ee04df40dc978199622f226cb1
Source dataset
uspto-grants-1977_12
Patent number
US04064132

Reaction notes

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