Methanol → (4-Chloro-3-fluoropyridin-2-yl)methanol

HRID 1655228Notes

Reaction equation

HRID 1655228 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].[CH3:14][C:15]1[C:20]([F:21])=[C:19]([Cl:22])[CH:18]=[CH:17][N+:16]=1[O-].CO>ClCCl>[OH:4][CH2:14][C:15]1[C:20]([F:21])=[C:19]([Cl:22])[CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 9845Trifluoroacetic anhydrideHCID 197911332-methyl-3-fluoro-4-chloro-pyridine-N-oxide

Product 1

HCID 19791242(4-Chloro-3-fluoropyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic anhydride (16.18 ml) was added dropwise at 10°-15° to a solution of 2-methyl-3-fluoro-4-chloropyridine-N-oxide (6.17 g) in dichloromethane (50 ml). After three days at room temperature, methanol (30 ml) was added to the cooled solution. The excess solvent was removed and the residue dissolved in water. After basifying (NaOH), the solution was extracted with dichoromethane. The extracts were dried (K2CO3) and evaporated to dryness to give a solid which was purified by column chromatography (silica gel; 1% MeOH/CHCl3) to give 2-hydroxymethyl-3-fluoro-4-chloropyridine (3.8 g) m.p. indeterminate)

Workup

  1. customThe excess solvent was removed
  2. dissolutionthe residue dissolved in water
  3. extractionthe solution was extracted with dichoromethane
  4. dry with materialThe extracts were dried (K2CO3)
  5. customevaporated to dryness
  6. customto give a solid which
  7. customwas purified by column chromatography (silica gel; 1% MeOH/CHCl3)

Sources & evidence

ORD record
ord-109071d2f9044740baaa969e9fe8ac1d
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

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