3,5-Dichloro-1-fluoropyridinium triflate → Methyl 5-fluoro-4-hydroxy-2-methoxybenzoate

HRID 1292038Notes

Reaction equation

HRID 1292038 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[F:14]C(F)(F)S([O-])(=O)=O.F[N+]1C=C(Cl)C=C(Cl)C=1>ClCCl>[F:14][C:11]1[C:2]([OH:1])=[CH:3][C:4]([O:12][CH3:13])=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 27245783,5-Dichloro-1-fluoropyridinium triflateHCID 12532676Methyl 4-hydroxy-2-methoxybenzoate

Product 1

HCID 18914108Methyl 5-fluoro-4-hydroxy-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 4-hydroxy-2-methoxybenzoate (10 g, 55 mmol) from step 3 above and 1-fluoro-3,5-dichloropyridinium trifluoromethanesulfonate (21 g, 66 mmol) were refluxed in dichloromethane (250 mL) for 48 h. The solution was washed with 5% aqueous citric acid (250 mL) and the organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 99:1 CH2Cl2 :MeOH as eluant. Crystallization from ether gave methyl 5-fluoro-4-hydroxy-2-methoxybenzoate.

Workup

  1. washThe solution was washed with 5% aqueous citric acid (250 mL)
  2. dry with materialthe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by pressurized silica gel column chromatography
  6. customCrystallization from ether

Sources & evidence

ORD record
ord-f121f80055ba45ab88dfc71a1e8d09ed
Source dataset
uspto-grants-1998_05
Patent number
US05756497

Reaction notes

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