Ethyl Acetate → 2,5-Difluoroaniline

HRID 1428630Notes

Reaction equation

HRID 1428630 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N+:9]([O-])=O.CC(=O)OCC>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH2:9]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 677672,5-Difluoronitrobenzene

Product 1

HCID 677752,5-DifluoroanilineYield 83.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 1,4-difluoro-2-nitrobenzene (500 mg, 3.14 mmol) in MeOH (20 mL) was added Pd/C (66.9 mg, 0.629 mmol) in portions. Then the mixture was stirred under a H2 atmosphere at 20° C. for 1 h. After TLC (PE/EA=3/1) analysis showed the starting material had disappeared, the mixture was filtered. The filtrate was concentrated to give the desired product 2,5-difluoroaniline (338 mg, 2.61 mmol, 83% yield). 1H NMR: (400 MHz, CDCl3) δ 6.94-6.88 (m, 1H), 6.50-6.46 (m, 1H), 6.40-6.31 (m, 1H), 3.82 (br. s., 2H).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6e83b218022f478e8b320c7835694df7
Source dataset
uspto-grants-2015_01
Patent number
US08937071B2

Reaction notes

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