Nitric Acid → 4-Fluoro-2-nitrophenol

HRID 1533879Notes

Reaction equation

HRID 1533879 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1>C(O)(=O)C>[F:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([N+:1]([O-:4])=[O:2])[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 97324-Fluorophenol

Product 1

HCID 1362364-Fluoro-2-nitrophenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mechanically stirred solution of 400 ml concentrated nitric acid, at 0° C., was added dropwise a solution of 4-fluorophenol (204 g, 1.8 mole) in acetic acid (200 ml) over 2 hours. Stirring was continued for another 2 hours at 5° C. The reaction mixture was poured onto ice, and the resulting yellow solids were collected and washed with water. The solids were recrystallized from methanol-water (5:1) to afford 198 g of the title compound. The NMR spectrum showed absorption at 7.17 (dd, 1H, J=9, 5 Hz), 7.44-7.52 (m, 1H) and 7.80 (dd, 1H, J=8, 3 Hz).

Workup

  1. additionThe reaction mixture was poured onto ice
  2. customthe resulting yellow solids were collected
  3. washwashed with water
  4. customThe solids were recrystallized from methanol-water (5:1)

Sources & evidence

ORD record
ord-1e742052b2c1456a9aabe83a74e97e38
Source dataset
uspto-grants-1992_02
Patent number
US05086062

Reaction notes

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