Sodium Hydroxide → 5-Fluoro-3-methoxy-2-nitrophenol

HRID 1372601Notes

Reaction equation

HRID 1372601 reaction equation
[OH-:1].[Na+].F[C:4]1[C:5]([N+:13]([O-:15])=[O:14])=[C:6]([O:11][CH3:12])[CH:7]=[C:8]([F:10])[CH:9]=1>CS(C)=O.Cl>[F:10][C:8]1[CH:7]=[C:6]([O:11][CH3:12])[C:5]([N+:13]([O-:15])=[O:14])=[C:4]([OH:1])[CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 103301291,5-Difluoro-3-methoxy-2-nitrobenzene

Product 1

HCID 184333835-Fluoro-3-methoxy-2-nitrophenolYield 51%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

In 10N NaOH (13.1 ml, 131 mmol) and DMSO (25 ml), 3,5-difluoro-2-nitroanisole (8.29 g, 43.8 mmol) was stirred at 50° C. for 5 hours. After cooling, the reaction mixture was poured in 1N HCl (200 ml), followed by extraction with ethyl acetate (300 ml). The extract was washed with saturated brine (2×100 ml), dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (4:1) eluate fractions, the title compound (4.14 g, 51%) was obtained as a yellow oil.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate (300 ml)
  3. washThe extract was washed with saturated brine (2×100 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by chromatography on a silica gel column, whereby from hexane-ethyl acetate (4:1) eluate fractions

Sources & evidence

ORD record
ord-e0dbe609fc754325a72346a2db1e8cf5
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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