Acetic Acid → 3-Chloro-4-fluoro-5-(trifluoromethyl)aniline

HRID 1188005Notes

Reaction equation

HRID 1188005 reaction equation
C(O)(=O)C.O.[Cl:6][C:7]1[CH:8]=[C:9]([N+:18]([O-])=O)[CH:10]=[C:11]([C:14]([F:17])([F:16])[F:15])[C:12]=1[F:13]>C(O)(=O)C.C(OCC)(=O)C>[Cl:6][C:7]1[CH:8]=[C:9]([CH:10]=[C:11]([C:14]([F:17])([F:15])[F:16])[C:12]=1[F:13])[NH2:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 299348431-Chloro-2-fluoro-5-nitro-3-(trifluoromethyl)benzene

Product 1

HCID 299348473-Chloro-4-fluoro-5-(trifluoromethyl)anilineYield 114%

Reagents, catalysts & solvents 1

HCID 22609514Ethyl acetate acetateSolvent

Procedure

In a mixture of 7.0 g of reduced iron, 4 mL of acetic acid and 50 mL of water, a solution of 6.0 g of 5-chloro-6-fluoro-3-nitrobenzotrifluoride in 80 mL of acetic acid-ethyl acetate (1:1) was added dropwise at 80° C. with stirring over 30 minutes. After the completion of the addition dropwise, it was continued to stir at the same temperature further for 1 hour. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, insoluble material was filtered off through Celite, the organic phase was collected and washed with 100 mL of water and then 100 mL of saturated sodium hydrogen carbonate aqueous solution. The organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 6.0 g of the crude aimed product as red-brown oily substance. The resulting product was used as such without purification for the next step.

Workup

  1. additionAfter the completion of the addition dropwise
  2. stirringto stir at the same temperature further for 1 hour
  3. customAfter the completion of the reaction
  4. waitthe reaction mixture was left
  5. filtrationinsoluble material was filtered off through Celite
  6. customthe organic phase was collected
  7. washwashed with 100 mL of water
  8. dry with materialdried over saturated sodium chloride aqueous solution
  9. distillationanhydrous sodium sulfate, and the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b291e411d6be48aa92294787b7b15c1f
Source dataset
uspto-grants-2014_03
Patent number
US08673951B2

Reaction notes

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