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(4-Nitro-2,6-difluoro-phenoxy)-acetic acid methyl ester → Methyl (4-amino-2,6-difluorophenoxy)acetate

HRID 1004080
Notes
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Reaction equation

HRID 1004080 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][O:5][C:6]1[C:11]([F:12])=[CH:10][C:9]([N+:13]([O-])=O)=[CH:8][C:7]=1[F:16].[H][H]>[Pd].O1CCCC1>[CH3:1][O:2][C:3](=[O:17])[CH2:4][O:5][C:6]1[C:7]([F:16])=[CH:8][C:9]([NH2:13])=[CH:10][C:11]=1[F:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 54234870(4-Nitro-2,6-difluoro-phenoxy)-acetic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 53642646Methyl (4-amino-2,6-difluorophenoxy)acetateYield 99.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A slurry of (4-nitro-2,6-difluoro-phenoxy)-acetic acid methyl ester (737 mg, 2.98 mmol) and 10% palladium on carbon (200 mg) in tetrahydrofuran (40 mL) was stirred under 1 atmosphere of hydrogen gas for 7 h. The mixture was flushed with nitrogen, and filtered through a pad of celite to afford the title compound as a pale tan oil (646 mg) that solidified on standing.

Workup

  1. customThe mixture was flushed with nitrogen
  2. filtrationfiltered through a pad of celite

Sources & evidence

ORD record
ord-e1ccb35760ea40a983a37601bd2ecd74
Source dataset
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06048872

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes