Thionyl Chloride → 6-[(4-Fluorophenyl)oxy]-3-pyridinecarbonyl chloride

HRID 534787Notes

Reaction equation

HRID 534787 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([C:15]([OH:17])=O)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:20])=O>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:14]=[CH:13][C:12]([C:15]([Cl:20])=[O:17])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 167905786-(4-fluorophenoxy)nicotinic acid

Product 1

HCID 231490426-[(4-Fluorophenyl)oxy]-3-pyridinecarbonyl chloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6-[(4-Fluorophenyl)oxy]-3-pyridinecarboxylic acid (D14) (0.032 g, 0.14 mmol) was solubilised in dry dioxane (2 mL). Thionyl chloride (0.081 mg, 0.14 mmol) was added drop-wise and the reaction mixture heated at reflux for 1.25 h. The reaction mixture was concentrated, and then re-concentrated from DCM to give 6-[(4-fluorophenyl)oxy]-3-pyridinecarbonyl chloride which was used directly in step 2

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 1.25 h
  3. concentrationThe reaction mixture was concentrated
  4. concentrationre-concentrated from DCM

Sources & evidence

ORD record
ord-04a1a786c902403eb64393baca723746
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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