Methanol → 3,6-Difluoro-2-methoxypyridine

HRID 912623Notes

Reaction equation

HRID 912623 reaction equation
F[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[N:3]=1.[CH3:10][OH:11].C[O-].[Na+]>O>[F:8][C:7]1[C:2]([O:11][CH3:10])=[N:3][C:4]([F:9])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 27832882,3,6-TrifluoropyridineHCID 10942334Sodium Methoxide

Product 1

HCID 669368673,6-Difluoro-2-methoxypyridineYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

step 1—To a flask containing 2,3,6-trifluoropyridine (2 g, 15 mmol) was added MeOH (5 mL) followed by methanolic NaOMe (5 mL, 25% NaOMe in MeOH). An exothermic reaction occurred and some solid formed. The reaction was stirred for 10 min and diluted with H2O. The solid was filtered and washed with H2O. The solid was dissolved in EtOAc, washed sequentially with water and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford 1.5 g (69%) of 3,6-difluoro-2-methoxy-pyridine (140). The recovered material was used without further purification.

Workup

  1. customAn exothermic reaction
  2. customsome solid formed
  3. filtrationThe solid was filtered
  4. washwashed with H2O
  5. dissolutionThe solid was dissolved in EtOAc
  6. washwashed sequentially with water and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5e41ce56efe4c93956efa441418dc15
Source dataset
uspto-grants-2011_09
Patent number
US08026253B2

Reaction notes

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