Ammonia → 3,5-difluoro-2-nitroaniline

HRID 547646Notes

Reaction equation

HRID 547646 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4](F)[C:3]=1[N+:10]([O-:12])=[O:11].[NH3:13]>O1CCCC1.CO>[F:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([CH:5]=[C:6]([F:8])[CH:7]=1)[NH2:13]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 675671,3,5-Trifluoro-2-nitrobenzene

Product 1

HCID 2230923,5-difluoro-2-nitroaniline

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the 1,3,5-trifluoro-2-nitrobenzene (7.08 g, 39.98 mmol) in tetrahydrofuran (50 mL) was stirred at 0 degrees Centigrade while a solution of 7N ammonia in methanol (23 mL) was added. The reaction turned deep red and was stirred overnight in a sealed tube. The mixture was filtered to remove NH4F and the solvent removed to give a red-orange solid which was purified by silica gel chromatography using 2:1 hexanes/ethyl acetate to give 6.27 g of 3,5-difluoro-2-nitroaniline.

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. customto remove NH4F
  4. customthe solvent removed
  5. customto give a red-orange solid which
  6. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-31446d4f5f564faf8ee20a534f43e213
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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