1-Ethoxy-2,5-difluoro-4-nitrobenzene → 4-Ethoxy-2,5-difluoroaniline

HRID 1811550Notes

Reaction equation

HRID 1811550 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([N+:11]([O-])=O)=[CH:6][C:5]=1[F:14])[CH3:2]>[Pd].C(O)C>[CH2:1]([O:3][C:4]1[C:5]([F:14])=[CH:6][C:7]([NH2:11])=[C:8]([F:10])[CH:9]=1)[CH3:2]

Participants

4

Reactant 1

HCID 685658171-Ethoxy-2,5-difluoro-4-nitrobenzene

Product 1

HCID 635998694-Ethoxy-2,5-difluoroanilineYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-ethoxy-2,5-difluoro-4-nitro-benzene (1.00 g, 4.92 mmol) and palladium on carbon (10%, 50% water, 307 mg) in ethanol (20 mL) were shaken in a hydrogenator under H2 atmosphere at 45 psi. After 30 minutes, solids were filtered off, washed with ethanol, and filtrate was concentrated to give 4-ethoxy-2,5-difluoro-phenylamine as a red solid (835 mg, 98%). 1HNMR (CDCl3, 400 MHz) δ 6.72-6.67 (m, 1H), 6.58-6.53 (m, 1H), 4.03-3.97 (q, J=7.0 Hz, 2H), 3.50 (s br, 2H), 1.41-1.37 (t, J=7.0 Hz, 3H). Exact mass calculated for C8H9F2NO 173.07 found 174.2 (MH+).

Workup

  1. filtrationsolids were filtered off
  2. washwashed with ethanol, and filtrate
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-583b7d8fc079445087fa35f31fe86135
Source dataset
uspto-grants-2013_01
Patent number
US08362248B2

Reaction notes

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