Dimethylformamide → 4-Fluoro-2-nitroanisole

HRID 1460566Notes

Reaction equation

HRID 1460566 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.[CH3:14]N(C=O)C>>[F:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:14])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 1362364-Fluoro-2-nitrophenol

Product 1

HCID 5656564-Fluoro-2-nitroanisole

Procedure

Sodium hydride 4.59 g (7.64 g as 60% mineral oil dispersion) was suspended in DMF (64 ml) under a nitrogen atmosphere. To this was added 4-fluoro-2-nitrophenol in 64 ml DMF over 30 minutes at room temperature. Stirring continued for 15 minutes. Methyl iode was then added over 15 minutes. The mixture was further stirred for 3 hours. The precipitates which formed were filtered off and the filtrate was evaporated to dryness. The residue was dissolved in benzene and the filtrate washed with water, aqueous sodium hydroxide and with brine. This solution was dried over sodium sulfate and evaporated to give 21.1 g of the title compound: m.p. 60° C.

Workup

  1. additionMethyl iode was then added over 15 minutes
  2. stirringThe mixture was further stirred for 3 hours
  3. customThe precipitates which
  4. customformed
  5. filtrationwere filtered off
  6. customthe filtrate was evaporated to dryness
  7. dissolutionThe residue was dissolved in benzene
  8. washthe filtrate washed with water, aqueous sodium hydroxide and with brine
  9. dry with materialThis solution was dried over sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-066f1bc236e843fa97f5f79c848c7fc3
Source dataset
uspto-grants-1991_12
Patent number
US05071863

Reaction notes

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