4-Bromo-2-fluoro-1-nitrobenzene → 5-Bromo-2-nitroanisole

HRID 871848Notes

Reaction equation

HRID 871848 reaction equation
F[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][O-:13].[Na+]>CO>[Br:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([O:13][CH3:12])[CH:7]=1

Participants

4

Reactant 2

HCID 27833624-Bromo-2-fluoro-1-nitrobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 117464905-Bromo-2-nitroanisoleYield 89.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

18.4 g (83.64 mmol) of 2-fluoro-4-bromonitrobenzene (Aldrich) are almost fully dissolved in 300 mL of anhydrous methanol. 19.9 mL (106.22 mmol) of a 30% solution of sodium methoxide in methanol are added dropwise and the mixture is stirred overnight at room temperature. The methanol is evaporated off under reduced pressure, the medium is taken up in ethyl acetate and water, and the aqueous phase is then acidified by adding aqueous 1N HCl. After separation of the phases by settling, the organic phase is washed with saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated under vacuum. 17.4 g of the expected product are obtained in the form of a yellow solid. Yield=89.7%.

Workup

  1. customThe methanol is evaporated off under reduced pressure
  2. additionby adding aqueous 1N HCl
  3. customAfter separation of the phases
  4. washthe organic phase is washed with saturated aqueous NaCl
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4dc00eb98c61481dba281c73dd4f88df
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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