2-Benzyloxy-4,5-difluoronitrobenzene → 2-(Benzyloxy)-4,5-difluoroaniline

HRID 660832Notes

Reaction equation

HRID 660832 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:10]=1[N+:17]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pt].C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:10]=1[NH2:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 688400302-Benzyloxy-4,5-difluoronitrobenzene

Product 1

HCID 688399052-(Benzyloxy)-4,5-difluoroaniline

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-benzyloxy-4,5-difluoronitrobenzene (2.35 g, 8.86 mmol) and 10% platinum on carbon (235 mg) in ethyl acetate (50 mL) is hydrogenated at atmospheric pressure for 6 h. The catalyst is filtered through Celite and solvent removed under reduced pressure. The residue is purified by silica gel chromatography on an Isco Companion using a gradient of 90:10 to 50:50 hexane/ethyl acetate to afford the title compound. 1H NMR (δ, CDCl3): 7.39 (m, 5H), 6.68 (dd, 1H, J=11.6, 7.3 Hz), 6.52 (dd, 1H, J=11.6, 7.8 Hz), 5.01 (s, 2H), 3.74 (br s, 2H). MS (M+1): 236.

Workup

  1. filtrationThe catalyst is filtered through Celite and solvent
  2. customremoved under reduced pressure
  3. customThe residue is purified by silica gel chromatography on an Isco Companion

Sources & evidence

ORD record
ord-f107095e5b8a407b859e9cdc8e635681
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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