4'-Chloro-4-chloromethylbiphenyl → 2-[4-(4-Chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionitrile

HRID 973298Notes

Reaction equation

HRID 973298 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:20]=[CH:19][C:18]([C:21]2[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=2)=[CH:17][CH:16]=1>CN(C)C=O.O>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:28]=[CH:27][C:24]([CH2:25][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:23][CH:22]=2)=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 127738464'-Chloro-4-chloromethylbiphenylHCID 867351682-Hydroxy-3,3,3-trifluoro-2-trifluoromethylpropionitrile sodium salt

Product 1

HCID 203144622-[4-(4-Chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-hydroxy-3,3,3-trifluoro-2-trifluoromethylpropionitrile sodium salt (4.3 g.) and 4-(4-chlorophenyl)-benzyl chloride (4.7 g.) in dimethylformamide (25 ml.) is stirred at ambient temperature for 10 days, then diluted with water. During this reaction, 2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionitrile is formed and is subsequently hydrolysed to the corresponding amide. The mixture is extracted with 1,2,2-trichloro-1,1,2-trifluoroethane, and the extract is dried with sodium sulphate, then evaporated. The residue is crystallised from cyclohexane to give 2-[4-(4-chlorophenyl)benzyloxy]-3,3,3-trifluoro-2-trifluoromethylpropionamide, m.p. 123°-124° C. (1.6 g.).

Workup

  1. customDuring this reaction

Sources & evidence

ORD record
ord-870e0a4859d441b59a63a61308d443be
Source dataset
uspto-grants-1977_10
Patent number
US04055595

Reaction notes

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