Thionyl Chloride → 6-(3-Fluorophenyl)-3-pyridinecarbonyl chloride

HRID 534742Notes

Reaction equation

HRID 534742 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([C:14]([OH:16])=O)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.S(Cl)([Cl:19])=O>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[CH:12][C:11]([C:14]([Cl:19])=[O:16])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 247299726-(3-Fluorophenyl)nicotinic acid

Product 1

HCID 866181106-(3-Fluorophenyl)-3-pyridinecarbonyl chlorideYield 99.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6-(3-Fluorophenyl)-3-pyridinecarboxylic acid (82 mg, 0.376 mmol) was stirred in dioxane (4 mL) and thionyl chloride (0.137 mL, 1.88 mmol) added dropwise. The reaction mixture was heated at reflux for 40 min then concentrated in vacuo to give 6-(3-fluorophenyl)-3-pyridinecarbonyl chloride as a white solid (0.088 g) which was used directly in step 2.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 40 min
  3. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-c4505d7185bb43ecbb62bf048c82df5f
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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