3,4-Dichlorobenzotrifluoride → Benzenamine, 4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluoro-

HRID 1731786Notes

Reaction equation

HRID 1731786 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[OH-].[K+].Cl[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=1[Cl:23]>CS(C)=O.O.ClCCl>[F:1][C:2]1[CH:8]=[C:7]([O:9][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[Cl:23])[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

7

Reactant 3

HCID 94813,4-DichlorobenzotrifluorideHCID 14797Potassium HydroxideHCID 27359194-Amino-3-fluorophenol

Product 1

HCID 15595105Benzenamine, 4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluoro-

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 7.1 g of 2-fluoro-4-hydroxyaniline and 3.7 g of potassium hydroxide (85% pure) in 25 ml of dimethylsulphoxide (DMSO) was heated to 80° C. and treated with a solution of 10.9 g of 1,2-dichloro-4-(trifluoromethyl)benzene in 10 ml of DMSO. The mixture was stirred at 90°-95° C. for 20 hours, after which it was diluted with a mixture of water and dichloromethane. The organic phase was dried (Na2SO4) and the solvent was evaporated. The residue was chromatographed over silica gel using a 4:1 v:v mixture of toluene and petroleum ether to give 31, as a yellow oil.

Workup

  1. dry with materialThe organic phase was dried (Na2SO4)
  2. customthe solvent was evaporated
  3. customThe residue was chromatographed over silica gel using a 4:1 v
  4. additionv mixture of toluene and petroleum ether

Sources & evidence

ORD record
ord-1f7ff719ad66457ba4acf22474d4e131
Source dataset
uspto-grants-1986_11
Patent number
US04623658

Reaction notes

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