Water → alpha-[2-(4-Bromophenoxy)ethyl]-2,4-dichlorobenzeneacetonitrile

HRID 745270Notes

Reaction equation

HRID 745270 reaction equation
O.[H-].[Na+].[Cl:4][C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:6]=1[CH2:12][C:13]#[N:14].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24]Br)=[CH:18][CH:17]=1>CS(C)=O>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH:12]([C:6]2[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:5]=2[Cl:4])[C:13]#[N:14])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 805662,4-DichlorophenylacetonitrileHCID 877972-Bromoethyl p-bromophenyl ether

Product 1

HCID 12393437alpha-[2-(4-Bromophenoxy)ethyl]-2,4-dichlorobenzeneacetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a stirred and cooled (water-bath) suspension of 7 parts of a sodium hydride dispersion 78% and 75 parts of dimethylsulfoxide is added dropwise, during a 30 minutes-period, a solution of 37 parts of 2,4-dichlorobenzeneacetonitrile in 100 parts of dimethylsulfoxide. The whole is stirred for 30 minutes while cooling in a water-bath. Then there is added dropwise, during a 30 minutes-period, a solution of 56 parts of 1-bromo-4-(2-bromoethoxy)benzene in 125 parts of dimethylsulfoxide and stirring is continued for another 30 minutes. The reaction mixture is poured onto water and the product is extracted twice with 2,2'-oxybispropane. The combined extracts are washed twice with water, dried, filtered and evaporated. The residue is triturated in petroleumether. The product is filtered off and crystallized from ethanol, yielding 38 parts of α-[2-(4-bromophenoxy)ethyl]-2,4-dichlorobenzeneacetonitrile; mp. 73.9° C.

Workup

  1. temperaturecooled
  2. additionis added dropwise, during a 30 minutes-period
  3. stirringThe whole is stirred for 30 minutes
  4. temperaturewhile cooling in a water-bath
  5. additionThen there is added dropwise, during a 30 minutes-period
  6. additionThe reaction mixture is poured onto water
  7. extractionthe product is extracted twice with 2,2'-oxybispropane
  8. washThe combined extracts are washed twice with water
  9. customdried
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue is triturated in petroleumether
  13. filtrationThe product is filtered off
  14. customcrystallized from ethanol

Sources & evidence

ORD record
ord-d84c1ce370d4472883985b6709fe71bb
Source dataset
uspto-grants-1986_07
Patent number
US04598085

Reaction notes

Loading…