Hydrochloric Acid → 4-(4-Trifluoromethoxyphenoxy)-3-trifluoromethylaniline

HRID 1361464Notes

Reaction equation

HRID 1361464 reaction equation
O.Cl.[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=2)=[C:8]([C:24]([F:27])([F:26])[F:25])[CH:7]=1)([O-])=O.O.C(=O)(O)[O-].[Na+]>C(O)C.[Fe]>[F:21][C:20]([F:22])([F:23])[O:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:9]2[CH:10]=[CH:11][C:6]([NH2:3])=[CH:7][C:8]=2[C:24]([F:25])([F:26])[F:27])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 860949224-Nitro-1-(4-trifluoromethoxyphenoxy)-2-trifluoromethylbenzeneHCID 86585896Sodium bicarbonate water

Product 1

HCID 860948674-(4-Trifluoromethoxyphenoxy)-3-trifluoromethylanilineYield 99.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Procedure

Iron powder (72.7 g), 251 mL of ethanol, 103 mL of distilled water, and 0.55 mL of 35% hydrochloric acid were mixed together, and the mixture was heated to reflux. Subsequently, a solution of 66.9 g of 4-nitro-1-(4-trifluoromethoxyphenoxy)-2-trifluoromethylbenzene dissolved in 77 mL of ethanol was added dropwise to the mixed solution, and the mixture was heated under reflux for 2.5 hr. The reaction solution was cooled to room temperature, sodium bicarbonate water was added thereto, and the mixture was filtered. The filtrate was concentrated under the reduced pressure, and ethyl acetate and brine were added to the residue, followed by separation. The ethyl acetate layer was washed with brine and was then concentrated under the reduced pressure to give 61.0 g of 4-(4-trifluoromethoxyphenoxy)-3-trifluoromethylaniline (yield 99%).

Workup

  1. temperaturethe mixture was heated to reflux
  2. additionwas added dropwise to the mixed solution
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 2.5 hr
  5. filtrationthe mixture was filtered
  6. concentrationThe filtrate was concentrated under the reduced pressure, and ethyl acetate and brine
  7. additionwere added to the residue
  8. customfollowed by separation
  9. washThe ethyl acetate layer was washed with brine
  10. concentrationwas then concentrated under the reduced pressure

Sources & evidence

ORD record
ord-a8229b671f1549b48309640ce674f7ee
Source dataset
uspto-grants-2011_02
Patent number
US07880006B2

Reaction notes

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