Hydrazine hydrate (1:1) → [2,6-Dichloro-3-fluoro-4-(trifluoromethyl)phenyl]hydrazine

HRID 2107882Notes

Reaction equation

HRID 2107882 reaction equation
[Cl:1][C:2]1[C:3]([F:14])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:5]=[C:6]([Cl:9])[C:7]=1F.O.[NH2:16][NH2:17]>C(O)C>[Cl:1][C:2]1[C:3]([F:14])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[NH:16][NH2:17]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 139134161,3-Dichloro-2,4-difluoro-5-(trifluoromethyl)benzene

Product 1

HCID 13913417[2,6-Dichloro-3-fluoro-4-(trifluoromethyl)phenyl]hydrazineYield 90.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

470 g (1.87 mol) of 3,5-dichloro-2,4-difluorobenzotrifluoride are initially introduced in 1000 ml of ethanol, 142 g (2.84 mol) of hydrazine hydrate are metered in, and the mixture is subsequently heated to reflux for 3 hours. The solvent is then removed by distillation under reduced pressure, and the residue is stirred into 1000 ml of cold water. After 30 minutes, the solid product is filtered off with suction and dried in a circulation dryer. 445 g (90% of theory) of 2,6-dichloro-3-fluoro-4-trifluoromethyl-phenylhydrazine of melting point 50° to 51° C. are obtained.

Workup

  1. temperatureis subsequently heated
  2. temperatureto reflux for 3 hours
  3. customThe solvent is then removed by distillation under reduced pressure
  4. filtrationthe solid product is filtered off with suction
  5. customdried in a circulation dryer

Sources & evidence

ORD record
ord-59a8f2daa4b248f5945d18defd0de022
Source dataset
uspto-grants-1990_06
Patent number
US04936892

Reaction notes

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