Hydrochloric Acid → 4-Amino-2-fluorobenzotrifluoride

HRID 648284Notes

Reaction equation

HRID 648284 reaction equation
Cl.[F:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].[OH-].[Na+]>C(O)C>[NH2:9][C:7]1[CH:6]=[CH:5][C:4]([C:12]([F:13])([F:14])[F:15])=[C:3]([F:2])[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 149414112-Fluoro-4-nitro-1-(trifluoromethyl)benzene

Product 1

HCID 27359144-Amino-2-fluorobenzotrifluoride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 20 ml of concentrated hydrochloric acid and 15 ml of 95% ethanol is added 5.0 g (24 mmole) of 2-fluoro,4-nitrobenzotrifluoride. The mixture is stirred and 20 g (88 mmole) of stannous chloride dihydrate is added in portions over a 30 min period. The reaction is exothermic and during the addition the temperature is maintained at 60°. When the addition is complete, the mixture is stirred at 60° for an additional 30 min. The reaction is cooled and poured onto a mixture of ice and 36% sodium hydroxide, which is extracted with ether (3×). The combined ether layers are washed once with brine and dried over sodium sulfate. Filtration and evaporation of the solvent gave 4-amino,2-fluorobenzotrifluoride (3-fluoro-4-trifluoromethylaniline).

Workup

  1. additionThe reaction is exothermic and during the addition the temperature
  2. temperatureis maintained at 60°
  3. additionWhen the addition
  4. stirringthe mixture is stirred at 60° for an additional 30 min
  5. temperatureThe reaction is cooled
  6. extractionis extracted with ether (3×)
  7. washThe combined ether layers are washed once with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-4f7d8402fc1c4e039dc69ed4b19246c4
Source dataset
uspto-grants-1983_10
Patent number
US04411912

Reaction notes

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