Thionyl Chloride → 2-Fluoro-isonicotinoyl chloride

HRID 1080684Notes

Reaction equation

HRID 1080684 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][N:3]=1.S(Cl)([Cl:13])=O>>[F:1][C:2]1[CH:7]=[C:6]([C:8]([Cl:13])=[O:10])[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 3453602-Fluoroisonicotinic acid

Product 1

HCID 143034342-Fluoro-isonicotinoyl chloride

Procedure

A mixture of the above 2-fluoropyridine-4-carboxylic acid (10 g) and thionyl chloride (70 mL) was heated at reflux for 25 hours. The excess thionyl chloride was removed by distillation at atmospheric pressure and the residue was distilled giving 9.51 grams of 2-fluoropyridine-4-carbonyl chloride having a boiling point of 88° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 25 hours
  3. customThe excess thionyl chloride was removed by distillation at atmospheric pressure
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-d1e10e2d89f34b1e8c4c05b301a2d252
Source dataset
uspto-grants-1996_12
Patent number
US05583148

Reaction notes

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