Methanol → Methyl 4,5-difluoro-2-nitrobenzoate

HRID 1172574Notes

Reaction equation

HRID 1172574 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.OS(O)(=O)=O.[CH3:20]O>>[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([O:8][CH3:20])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 42196304,5-Difluoro-2-nitrobenzoic acid

Product 1

HCID 21928432Methyl 4,5-difluoro-2-nitrobenzoate

Procedure

To a solution of 4,5-difluoro-2-nitrobenzoic acid 1a (40.0 g, 196.947 mmol) in anhydrous MeOH (1.0 L), was added concentrated H2SO4 (60.0 mL) and the clear mixture was refluxed for 2 days. Then methanol was removed in vacuo and the residue was partitioned between EtOAc and water. The EtOAc extract was washed with brine, dried over with anhydrous. Na2SO4, and concentrated to yield the methyl 4,5-difluoro-2-nitrobenzoate 1b as a pale yellow solid, 39.71 g (93%).

Workup

  1. temperaturethe clear mixture was refluxed for 2 days
  2. customThen methanol was removed in vacuo
  3. customthe residue was partitioned between EtOAc and water
  4. extractionThe EtOAc extract
  5. washwas washed with brine
  6. customdried over with anhydrous
  7. concentrationNa2SO4, and concentrated

Sources & evidence

ORD record
ord-296ed7a30b4b45768c7837a3414a43fc
Source dataset
uspto-grants-2010_11
Patent number
US07834023B2

Reaction notes

Loading…