2,2,2-Trifluoroethanol → HCID 87426689, compound

HRID 623467Notes

Reaction equation

HRID 623467 reaction equation
[Cl:1][C:2]1[N:10]=[C:9](Cl)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CC(C)([O-])C.[K+].[F:18][C:19]([F:23])([F:22])[CH2:20][OH:21]>>[Cl:1][C:2]1[N:10]=[C:9]([O:21][CH2:20][C:19]([F:23])([F:22])[F:18])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 8540472,6-Dichloronicotinic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 87426689HCID 87426689, compound

Procedure

A mixture of 2,6-dichloronicotinic acid (3.0 g, 15.6 mmol) and potassium tert-butoxide (5.26 g, 46.9 mmol) in 2,2,2-trifluoroethanol (52 mL) is refluxed with stirring for 5 days. After removal of solvent, the residue is dissolved in water (40 mL) then 2M hydrochloric acid (10 mL) is added. White precipitate is filtrated and dried to give 4.08 g of the title compound including 6-chloro-2-(2,2,2-trifluoroethoxy)nicotinic acid and 2,6-bis(2,2,2-trifluoroethoxy)nicotinic acid as a white solid. This material is used for the next reaction (Step-2) without further purification.

Workup

  1. temperatureis refluxed
  2. customAfter removal of solvent
  3. dissolutionthe residue is dissolved in water (40 mL)
  4. addition2M hydrochloric acid (10 mL) is added
  5. filtrationWhite precipitate is filtrated
  6. customdried

Sources & evidence

ORD record
ord-5456175244ba48318c3a4ec4fae460f9
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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