3,4-Difluoroaniline → 4-Fluoro-3-methoxyaniline

HRID 369265Notes

Reaction equation

HRID 369265 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].[CH3:10][O-:11].[Na+]>CO>[F:9][C:8]1[CH:7]=[CH:6][C:4]([NH2:5])=[CH:3][C:2]=1[O:11][CH3:10]

Participants

4

Conditions

Temperature
110 °C

Procedure

3,4-Difluoroaniline (2.6 g) was added to a 28% methanol solution of sodium methoxide, and the mixture was heated for 2 days at about 60° C. and for 4 days at 110° C. After distilled water (50 ml) was added to the reaction mixture, it was extracted with chloroform (50 ml). A chloroform layer was washed with distilled water (20 ml) and then dried over anhydrous magnesium sulfate. The dry chloroform layer was concentrated under reduced pressure to obtain the title compound (2.8 g) as a dark brown oil.

Workup

  1. distillationAfter distilled water (50 ml)
  2. additionwas added to the reaction mixture, it
  3. extractionwas extracted with chloroform (50 ml)
  4. washA chloroform layer was washed with distilled water (20 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe dry chloroform layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a9a243efab8740bd8529804fcd23aefd
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

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