Benzene, 1-(1,1-difluoroethoxy)-4-nitro- → Benzenamine, 4-(1,1-difluoroethoxy)-

HRID 73798Notes

Reaction equation

HRID 73798 reaction equation
[F:1][C:2]([F:14])([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1)[CH3:3]>CCO.[Ni]>[F:1][C:2]([F:14])([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[CH3:3]

Participants

4

Reactant 1

HCID 12101858Benzene, 1-(1,1-difluoroethoxy)-4-nitro-

Product 1

HCID 68195912Benzenamine, 4-(1,1-difluoroethoxy)-

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(1,1-difluoroethoxy)-4-nitrobenzene (Stage 30.4, 2.95 g, 13.94 mmol) in EtOH (100 mL) was hydrogenated (Raney Ni 1.0 g; 26.5 h at RT). The RM was filtered through Hyflo® and the solvent was evaporated off under reduced pressure to give the crude title product as a brown oil. HPLC (Condition 5) tR=4.5 min, UPLC-MS (Condition 3) tR=0.74 min, m/z=174.1 [M+H]+.

Workup

  1. filtrationThe RM was filtered through Hyflo®
  2. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-56d89adc9013488ca79558780be0c276
Source dataset
uspto-grants-2014_09
Patent number
US08829195B2

Reaction notes

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