Water → (6-Fluoropyridin-3-yl)methanol

HRID 1630734Notes

Reaction equation

HRID 1630734 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([F:9])=[N:7][CH:8]=1.Cl[CH:11](Cl)[C:12]1[CH:13]=[CH:14][C:15]([F:18])=[N:16][CH:17]=1.[C:20]([O-:23])([O-])=[O:21].[K+].[K+].[OH2:26]>>[F:9][C:6]1[N:7]=[CH:8][C:3]([CH2:2][OH:21])=[CH:4][CH:5]=1.[F:18][C:15]1[N:16]=[CH:17][C:12]([CH2:11][O:26][C:6]2[CH:5]=[CH:4][C:3]([CH:20]=[O:23])=[CH:8][N:7]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 190020735-(Dichloromethyl)-2-fluoropyridineHCID 220528815-(Chloromethyl)-2-fluoropyridine

Product 2

HCID 22663702(6-Fluoropyridin-3-yl)methanolHCID 584432816-((6-Fluoropyridin-3-yl)methoxy)nicotinaldehyde

Procedure

The mixture of 5-(chloromethyl)-2-fluoropyridine and 5-(dichloromethyl)-2-fluoropyridine (30.7 g, 211 mmol) was placed into a round-bottomed flask with H2O (300 mL) and K2CO3 (32.1 g, 232 mmol), which was heated to an oily suspension for 4 h. The mixture was then cooled to rt, and the layers were separated. The aqueous layer was washed with EtOAc (2×50 mL). The combined organic layers were then washed with H2O (3×100 mL), dried over MgSO4, filtered, and concentrated. This mixture was purified by column chromatography (6:1 hexane:EtOAc) to yield (6-fluoropyridin-3-yl)methanol and 6-((6-fluoropyridin-3-yl)methoxy)nicotinaldehyde.

Workup

  1. temperaturewas heated to an oily suspension for 4 h
  2. customthe layers were separated
  3. washThe aqueous layer was washed with EtOAc (2×50 mL)
  4. washThe combined organic layers were then washed with H2O (3×100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThis mixture was purified by column chromatography (6:1 hexane:EtOAc)

Sources & evidence

ORD record
ord-352a28de1eb4433fa1e41c57fc5d77f8
Source dataset
uspto-grants-2014_07
Patent number
US08791147B2

Reaction notes

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