Sodium Hydroxide → 4-Fluoro-2-methyl-5-nitrophenol

HRID 7498Notes

Reaction equation

HRID 7498 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([O:11]C(OC)=O)=[CH:6][C:5]=1[N+:16]([O-:18])=[O:17]>CO>[F:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([OH:11])=[CH:6][C:5]=1[N+:16]([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 144216192-Fluoro-5-methoxycarbonyloxy-4-methylnitrobenzene

Product 1

HCID 108210594-Fluoro-2-methyl-5-nitrophenolYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The starting material 2-fluoro-5-hydroxy-4-methylnitrobenzene, was obtained by adding 2M aqueous sodium hydroxide solution (13.1 ml), dropwise, to a solution of 2-fluoro-5-methoxycarbonyloxy-4-methylnitrobenzene (6 g, 26 mmol), (prepared as described in European Patent Publication No. 307777), in methanol (70 ml) cooled at 0° C. After stirring for 30 minutes, the mixture was concentrated by evaporation. After dilution with water, the solution was adjusted to pH2 and extracted with ethyl acetate. The organic layer was washed with water and then brine, dried (MgSO4) and the solvent evaporated to give 2-fluoro-5-hydroxy-4-methylnitrobenzene as a yellow solid (4 g, 90%).

Workup

  1. concentrationthe mixture was concentrated by evaporation
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialbrine, dried (MgSO4)
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-eb93562e983447698dff568eaa5a224c
Source dataset
uspto-grants-2006_08
Patent number
US07087602B2

Reaction notes

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