Nitric Acid → 4,5-Difluoro-2-nitrophenol

HRID 496194Notes

Reaction equation

HRID 496194 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].[N+:10]([O-])([OH:12])=[O:11]>C(O)(=O)C>[F:8][C:7]1[C:2]([F:1])=[CH:3][C:4]([OH:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 759273,4-Difluorophenol

Product 1

HCID 27741824,5-Difluoro-2-nitrophenolYield 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

In a flask was dissolved 3,4-Difluorophenol (3.10 g, 23.7 mmole) in acetic acid (15 ml). To the stirred solution was added dropwise a solution of fuming HNO3 (1.25 g, 29.7 mmole) in acetic acid (6 ml). The temperature was kept under 50° C. during the entire addition. After completed addition, the mixture was stirred for another hour. The reaction mixture was then poured onto ice-water, giving precipitation of a yellowish solid. The solid was collected by filtration, and dried. The solid was purified on silica (Heptane:EtOAc 5:1), giving the sub-title compound (2.05 g, 50%) as a yellow oil, which crystallizes on standing.

Workup

  1. additionThe temperature was kept under 50° C. during the entire addition
  2. additionaddition
  3. additionThe reaction mixture was then poured onto ice-water
  4. customgiving
  5. customprecipitation of a yellowish solid
  6. filtrationThe solid was collected by filtration
  7. customdried
  8. customThe solid was purified on silica (Heptane:EtOAc 5:1)

Sources & evidence

ORD record
ord-e1d53f02490a4e15b183f63779a43237
Source dataset
uspto-grants-2005_09
Patent number
US06943188B2

Reaction notes

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