Ammonia → 3,5-Difluoroaniline

HRID 1739543Notes

Reaction equation

HRID 1739543 reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][C:5](F)=[CH:4][C:3]=1[F:10].O.FC1C=C(F)C=C(F)C=1.[NH3:21]>[Cu].CO>[F:10][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([F:8])[CH:2]=1)[NH2:21]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 97451,3,5-Trifluorobenzene2×HCID 27366621-Chloro-2,4,6-trifluorobenzene

Product 1

HCID 965953,5-Difluoroaniline

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent

Procedure

EP 460 639 describes a three-stage preparation of 3,5-difluoroaniline. Starting from 5-chloro-2,4,6-trifluoroisophthalic acid, this is decarboxylated to give 2-chloro-1,3,5-trifluorobenzene. By reaction of the 2-chloro-1,3,5-trifluorobenzene with copper and water at 300° C., 1,3,5-trifluorobenzene can be prepared. According to Example 6 of EP 460 639, 1,3,5-tri-fluorobenzene is reacted with methanol saturated with ammonia at 200° C. for 60 hours and 3,5-difluoroaniline is obtained.

Sources & evidence

ORD record
ord-0d54714d55fc415d90690e5224e1cfbf
Source dataset
uspto-grants-1999_10
Patent number
US05965775

Reaction notes

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