Sulfuric Acid → 5-Fluoro-2-nitrophenol

HRID 483911Notes

Reaction equation

HRID 483911 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[OH-].[Li+].[Si](=O)=[O:15].S(=O)(=O)(O)O>O>[N+:9]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[OH:15])([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3939Lithium HydroxideHCID 24261SilicaHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 99375-Fluoro-2-nitrophenolYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

59.1 g (1 mol) of 2,4-difluoronitrobenzene and 300 g of water are initially introduced and 52.7 g (2.2 mol) of 50% strength lithium hydroxide solution are added dropwise at 45° C. The temperature is allowed to rise to 55° C. as a result of the exothermic reaction. After the end of this addition (5 hours) 60.1 g of silicon dioxide (Aerosil) are added and the pH is adjusted to 1.5 with sulfuric acid. The product is distilled over by the introduction of steam and isolated as described in example 1. 115.5 g (0.735 mol, 74% of theory) of 2-nitro-5-fluorophenol are obtained, which do not differ from the material prepared by example 1 with respect to purity.

Workup

  1. customto rise to 55° C.
  2. customa result of the exothermic reaction
  3. additionare added
  4. distillationThe product is distilled over by the introduction of steam
  5. customisolated

Sources & evidence

ORD record
ord-f7e6da20d7eb47589fb859741bdd861d
Source dataset
uspto-grants-1993_07
Patent number
US05227535

Reaction notes

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