1-Fluoro-4-(4-nitrophenoxy)-2-(trifluoromethyl)benzene → 4-[4-Fluoro-3-(trifluoromethyl)phenoxy]aniline

HRID 901675Notes

Reaction equation

HRID 901675 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19]>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=2)=[CH:4][C:3]=1[C:18]([F:19])([F:20])[F:21]

Participants

4

Reactant 1

HCID 669776401-Fluoro-4-(4-nitrophenoxy)-2-(trifluoromethyl)benzene

Product 1

HCID 669773444-[4-Fluoro-3-(trifluoromethyl)phenoxy]aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The nitro intermediate (2 mmol) obtained above was dissolved in MeOH (10 mL) and hydrogenated in the presence of 10% Pd/C (10 mg) until completion, as indicated by TLC or HPLC, according to General Procedure H. The reaction mixture was then filtered to remove the catalyst. The solvent was removed in vacuuo to afford the desired 4-[4-fluoro-3-(trifluoromethyl)phenoxy]aniline, which was used directly for further transformation without further purification.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customto remove the catalyst
  3. customThe solvent was removed in vacuuo

Sources & evidence

ORD record
ord-8e5d6b4462794c5aa29fa7d84833e590
Source dataset
uspto-grants-2008_04
Patent number
US07361678B2

Reaction notes

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