Methanol → 1-Fluoro-3-methoxy-2-nitrobenzene

HRID 2117038Notes

Reaction equation

HRID 2117038 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[C:3]=1[N+:9]([O-:11])=[O:10].[OH-:12].[K+].O.[CH3:15]O>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:12][CH3:15])[C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14797Potassium HydroxideHCID 879221,3-Difluoro-2-nitrobenzene

Product 1

HCID 27827761-Fluoro-3-methoxy-2-nitrobenzeneYield 95%

Procedure

To a solution of 2,6-difluoronitrobenzene (5 g, 32 mmol) in methanol (50 mL) was added potassium hydroxide (1.8 g, 32.5 mmol), and the mixture was heated to reflux for 3 hr. Water was added, and the mixture was extracted with dichloromethane. The organic layer was separated, dried, filtered, and evaporated to yield 5.1 g (95%) of 1-fluoro-3-methoxy-2-nitrobenzene, 1e. MS m/z (MH+) 172.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hr
  3. extractionthe mixture was extracted with dichloromethane
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-ad832688bbae49d49e44386af953bb88
Source dataset
uspto-grants-2008_10
Patent number
US07439239B2

Reaction notes

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