Methanol → Methyl 2,3-difluoro-4-methylbenzoate

HRID 1046667Notes

Reaction equation

HRID 1046667 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:13]O.S(=O)(=O)(O)O>>[CH3:13][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([CH3:12])=[C:10]([F:11])[C:2]=1[F:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27741412,3-Difluoro-4-methylbenzoic acid

Product 1

HCID 55255640Methyl 2,3-difluoro-4-methylbenzoateYield 83.2%

Procedure

2,3-Difluoro-4-methyl-benzoic acid (10.0 g, 58.1 mmol) was dissolved in MeOH (200 mL, 6.0 mol) and sulfuric acid (1.00 mL, 19.0 mmol), and was heated at reflux overnight. The mixture was then cooled and concentrated under reduced pressure. The resulting residue was taken up in EtOAc and washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated to yield 9.0 g of intermediate (7a) as a white solid. 1H-NMR (CDCl3): 7.61 (1H, t), 7.00 (1H, t), 3.93 (3H, s), 2.35 (3H, s).

Workup

  1. temperatureat reflux overnight
  2. temperatureThe mixture was then cooled
  3. concentrationconcentrated under reduced pressure
  4. washwashed with saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3f8fc90932ba481e893c2592948f7681
Source dataset
uspto-grants-2013_10
Patent number
US08569351B2

Reaction notes

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