4-(4-Fluorophenoxy)-3,5-difluoronitrobenzene → 4-(4-Fluorophenoxy)-3,5-difluoroaniline

HRID 1669984Notes

Reaction equation

HRID 1669984 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[C:12]([F:13])=[CH:11][C:10]([N+:14]([O-])=O)=[CH:9][C:8]=2[F:17])=[CH:4][CH:3]=1>[Pd].CCOC(C)=O>[F:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[C:12]([F:13])=[CH:11][C:10]([NH2:14])=[CH:9][C:8]=2[F:17])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 575886774-(4-Fluorophenoxy)-3,5-difluoronitrobenzene

Product 1

HCID 549028104-(4-Fluorophenoxy)-3,5-difluoroanilineYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(4-fluorophenoxy)-3,5-difluoronitrobenzene (30.4 g, 113 mmol), EtOAc (300 ml), 10% Pd/C (2.6 g) was stirred under an atmosphere of H2 at room temperature and pressure for approximately 6 hrs. The reaction mixture was filtered through Celite and concentrated in vacuo to give 4-(4-fluorophenoxy)-3,5-difluoroaniline (26.5 g, 98%) which was used in the next step without further purification. 1H NMR (CDCl3): δ 3.82 (s, 2H), 6.26 (d, 2H, J=8.4 Hz), 6.88 (m, 2H), 6.93 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bfa947f0934548b49b43ee6a1fa6b552
Source dataset
uspto-grants-2011_08
Patent number
US07989661B2

Reaction notes

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