4-Bromo-2,5-difluoronitrobenzene → 1-Bromo-2-fluoro-5-methoxy-4-nitrobenzene

HRID 2283511Notes

Reaction equation

HRID 2283511 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[F:12].[CH3:13][O-:14].[Na+]>CO>[Br:1][C:2]1[CH:7]=[C:6]([O:14][CH3:13])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[F:12]

Participants

4

Reactant 2

HCID 27362864-Bromo-2,5-difluoronitrobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 223473121-Bromo-2-fluoro-5-methoxy-4-nitrobenzeneYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1-bromo-2,5-difluoro-4-nitrobenzene (2.56 g, 0.011 mmol) in methanol (20 mL) was added a 25% sodium methoxide in methanol solution (2.5 mL). The mixture was stirred at room temperature for 1.5 hours. The reaction was then concentrated, re-dissolved in EtOAc and washed with water. The aqueous wash was back-extracted with EtOAc. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to give 1-bromo-2-fluoro-5-methoxy-4-nitrobenzene (2.65 g, 99%).

Workup

  1. concentrationThe reaction was then concentrated
  2. dissolutionre-dissolved in EtOAc
  3. washwashed with water
  4. washThe aqueous wash
  5. extractionwas back-extracted with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1d0cb8de55fb4a0bbbad0df971de26e6
Source dataset
uspto-grants-2015_09
Patent number
US09145402B2

Reaction notes

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