1-Fluoro-4-[(4-nitrophenoxy)methyl]benzene → 4-(4-Fluoro-benzyloxy)-phenylamine

HRID 453937Notes

Reaction equation

HRID 453937 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.[Ni]>[F:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 9575111-Fluoro-4-[(4-nitrophenoxy)methyl]benzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 64860214-(4-Fluoro-benzyloxy)-phenylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

1-Nitro-4-(4-fluorobenzyloxy)-benzene (2.37 g) was dissolved in 200 ml of methanol and catalytic amount of Raney Ni was added. The mixture was stirred at room temperature under atmospheric pressure in a hydrogen atmosphere for 3 hours. After filtering off Raney Ni over Celite and washing with methanol, the obtained filtrate was concentrated under reduced pressure to give a solid product 4-(4-fluoro-benzyloxy)-aniline, which is pure enough for next step.

Workup

  1. filtrationAfter filtering off Raney Ni over Celite
  2. washwashing with methanol
  3. concentrationthe obtained filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2818ef91f43543259ff50ce62216cba6
Source dataset
uspto-grants-2013_07
Patent number
US08492588B2

Reaction notes

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