Citric Acid → 5-Chloro-3-(trifluoromethyl)-1-benzothiophene-2-carboxylic acid

HRID 409912Notes

Reaction equation

HRID 409912 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[S:6][C:7]([C:13]([O:15]C)=[O:14])=[C:8]([C:9]([F:12])([F:11])[F:10])[C:4]=2[CH:3]=1.[Li+].[OH-].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO.O>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[S:6][C:7]([C:13]([OH:15])=[O:14])=[C:8]([C:9]([F:12])([F:11])[F:10])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3939Lithium HydroxideHCID 59625756HCID 59625756, compound

Product 1

HCID 591641865-Chloro-3-(trifluoromethyl)-1-benzothiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of compound 18e (574 mg, 1.95 mmol) and LiOH (187 mg, 7.80 mmol) in THF/MeOH/H2O (4/4/4 mL) was stirred for 4 h. A 15% citric acid solution (20 mL) was added, and the mixture was then extracted with EtOAc (3×). The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue, compound 18f, was dried under reduced pressure for 18 h and was used without purification.

Workup

  1. extractionthe mixture was then extracted with EtOAc (3×)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dry with materialThe residue, compound 18f, was dried under reduced pressure for 18 h
  7. customwas used without purification

Sources & evidence

ORD record
ord-9a56a0be310e494c9050d49de25b7e39
Source dataset
uspto-grants-2014_06
Patent number
US08759533B2

Reaction notes

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