1-Chloro-4-(chloromethyl)benzene → 2-(4-Chlorobenzyloxy)-3,3,3-trifluoro-2-trifluoromethylpropionitrile

HRID 973293Notes

Reaction equation

HRID 973293 reaction equation
[Na].[OH:2][C:3]([C:10]([F:13])([F:12])[F:11])([C:6]([F:9])([F:8])[F:7])[C:4]#[N:5].[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1>CN(C)C=O>[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][O:2][C:3]([C:6]([F:7])([F:9])[F:8])([C:10]([F:11])([F:12])[F:13])[C:4]#[N:5])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 867351682-Hydroxy-3,3,3-trifluoro-2-trifluoromethylpropionitrile sodium salt

Product 1

HCID 133842982-(4-Chlorobenzyloxy)-3,3,3-trifluoro-2-trifluoromethylpropionitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-hydroxy-3,3,3-trifluoro-2-trifluoromethylpropionitrile sodium salt (43 g.), 4-chlorobenzyl chloride (25.6 g.) and dimethylformamide (200 ml.) is stirred at ambient temperature for 5 days, then evaporated in vacuo. Water is added to the residue, and the mixture is extracted with 1,2,2-trichloro-1,1,2-trifluoroethane. The extract is dried with sodium sulphate, and evaporated. The residue is distilled to give 2-(4-chlorobenzyloxy)-3,3,3-trifluoro-2-trifluoromethylpropionitrile, b.p. 54°-64° C. at 1 mm. pressure (41.0 g.).

Workup

  1. customevaporated in vacuo
  2. additionWater is added to the residue
  3. extractionthe mixture is extracted with 1,2,2-trichloro-1,1,2-trifluoroethane
  4. dry with materialThe extract is dried with sodium sulphate
  5. customevaporated
  6. distillationThe residue is distilled

Sources & evidence

ORD record
ord-fc94466bb5454692a527a11534977d40
Source dataset
uspto-grants-1977_10
Patent number
US04055595

Reaction notes

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