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

HRID 534732Notes

Reaction equation

HRID 534732 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 chlorideYield 100.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6-[(4-Fluorophenyl)oxy]-3-pyridinecarboxylic acid (D14) (0.232 g, 0.994 mmol) was dissolved in 1,4-dioxane (6 mL) and thionyl chloride (0.363 mL, 4.972 mmol) added dropwise. The mixture was heated at reflux for 3.5 h, then cooled and concentrated in vacuo. DCM was added to the residue which was then re-concentrated to yield 6-[(4-fluorophenyl)oxy]-3-pyridinecarbonyl chloride as a yellow oil (0.252 g) which was used directly in step 2.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3.5 h
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. additionDCM was added to the residue which
  6. concentrationwas then re-concentrated

Sources & evidence

ORD record
ord-b5041b7932394b8ca2d7a90f3f5685f1
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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