2-Fluoro-4-(4-fluoro-benzyloxy)-nitrobenzene → 2-Fluoro-4-(4-fluoro-benzyloxy)-phenylamine

HRID 2225393Notes

Reaction equation

HRID 2225393 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>C(O)(=O)C.O.[Fe]>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 1

HCID 221379402-Fluoro-4-(4-fluoro-benzyloxy)-nitrobenzene

Product 1

HCID 221378852-Fluoro-4-(4-fluoro-benzyloxy)-phenylamineYield 70.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 11.0 g (0.041 mole) of 4-fluorophenylmethyl 3-fluoro-4-nitrophenyl ether in 100 mL of glacial acetic acid and 10 mL of water was heated to 50° C. To this hot solution was added 10.0 g (0.18 mole) of powdered iron. The reaction mixture was allowed to cool to ambient temperature, where it stirred for an additional hour. The reaction mixture was filtered through a bed of Celite® filter aid, and the Celite bed was washed in succession with ethyl acetate and 200 mL of water. The washes and the filtrate were combined, and the organic phase was separated. The organic phase was dried with anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure, leaving a dark oil as a residue. This oil was placed on a silica gel column and eluted with methylene chloride. The product-containing fractions were combined and the solvent evaporated under reduced pressure, leaving 6.8 g of 4-fluorophenylmethyl 4-amino-3-fluorophenyl ether as a solid, m.p. 42°-43° C.

Workup

  1. filtrationThe reaction mixture was filtered through a bed of Celite®
  2. filtrationfilter aid
  3. washthe Celite bed was washed in succession with ethyl acetate and 200 mL of water
  4. customthe organic phase was separated
  5. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customleaving a dark oil as a residue
  9. washeluted with methylene chloride
  10. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-a67ac49c466c4e178696509ba7246d89
Source dataset
uspto-grants-1994_09
Patent number
US05344812

Reaction notes

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