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

HRID 1746859Notes

Reaction equation

HRID 1746859 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-9ab87b8ccecd4e6bbd09ea35f10fbf39
Source dataset
uspto-grants-2015_10
Patent number
US09150514B2

Reaction notes

Loading…