Thionyl Chloride → 3,5-Difluoropyridine-2-carbonyl chloride

HRID 570514Notes

Reaction equation

HRID 570514 reaction equation
[F:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.S(Cl)([Cl:14])=O>>[F:1][C:2]1[C:3]([C:9]([Cl:14])=[O:11])=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 27832623,5-Difluoropyridine-2-carboxylic acid

Product 1

HCID 866606483,5-Difluoropyridine-2-carbonyl chloride

Procedure

A suspension of 5.00 g (31.4 mmol) of 3,5-difluoropyridine-2-carboxylic acid in thionyl chloride (21 ml) was heated to reflux for 5 h. The solution was concentrated, and the residue was twice taken up in a little toluene and concentrated again. This gave 3.80 g of a solid, which was converted further directly without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 h
  3. concentrationThe solution was concentrated
  4. concentrationconcentrated again
  5. customThis gave 3.80 g of a solid, which was converted further directly without further purification

Sources & evidence

ORD record
ord-b14b5d4b849e4272903e530b7f329717
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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