Dimethylformamide → Methyl 2,3-difluoro-4-methoxybenzoate

HRID 1007343Notes

Reaction equation

HRID 1007343 reaction equation
IC.[F:3][C:4]1[C:12]([F:13])=[C:11](O)[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7].[C:15](=O)([O-])[O-].[Li+].[Li+].CN(C)[CH:23]=[O:24]>O>[F:3][C:4]1[C:12]([F:13])=[C:11]([O:24][CH3:23])[CH:10]=[CH:9][C:5]=1[C:6]([O:8][CH3:15])=[O:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11125Lithium CarbonateHCID 27793072,3-difluoro-4-hydroxybenzoic acid

Product 1

HCID 21907384Methyl 2,3-difluoro-4-methoxybenzoateYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Iodomethane (10.7 mL, 172.5 mmol) was added into a mixture of 2,3-difluoro-4-hydroxybenzoic acid (10.0 g, 57.5 mmol), lithium carbonate (12.7 g, 172.5 mmol) and N,N-dimethylformamide (100 mL). The mixture was stirred at 40° C. for 12 h, and then poured into water and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (hexanes/EtOAc 5/1) gave a white solid (10.2 g, 88% yield, m.p. 66-68° C.); MS m/e 203 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic extracts were dried over MgSO4
  3. customEvaporation and purification by flash chromatography (hexanes/EtOAc 5/1)

Sources & evidence

ORD record
ord-e68cf4e779824eee8798035913fc8bda
Source dataset
uspto-grants-2004_09
Patent number
US06794403B2

Reaction notes

Loading…