Thionyl Chloride → 3-Fluoropyridine-2-carbonyl chloride

HRID 1497689

Reaction equation

HRID 1497689 reaction equation
[F:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[CH:6][CH:7]=1.S(Cl)([Cl:13])=O>C1(C)C=CC=CC=1>[F:1][C:2]1[C:3]([C:8]([Cl:13])=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27627863-Fluoropyridine-2-carboxylic acid

Product 1

HCID 861023073-Fluoropyridine-2-carbonyl chlorideYield 98.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 3-fluoropicolinic acid (4.23 g, 30 mmol) and thionyl chloride (35.7 g, 21.9 ml, 300 mmol) was heated to reflux for 15 h at which time it became a dark brown solution. Then, the heating was stopped and the reaction mixture was allowed to cool to room temperature and it was diluted with toluene. Then, the solvent and excess thionyl chloride were removed under vacuum. The residue was azeotrophed one more time with toluene and the resulting brown residue was dried under high vacuum to obtain 3-fluoropicolinoyl chloride (30) (4.70 g, 98.2% yield) as a brown paste which was used directly in the next step.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 15 h at which time it
  3. customThen, the solvent and excess thionyl chloride were removed under vacuum
  4. customthe resulting brown residue was dried under high vacuum

Sources & evidence

ORD record
ord-d54e54cf1b3b47cf9f8f49fe0661e844
Source dataset
uspto-grants-2015_12
Patent number
US09199987B2

Linked notes

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