Lithium Hydroxide → 5-Chloro-3-(trifluoromethyl)-1-benzothiophene-2-carboxylic acid

HRID 403291Notes

Reaction equation

HRID 403291 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-]>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

4

Reactant 2

HCID 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 11e (390 mg, 1.33 mmol) and LiOH (159 mg, 6.65 mmol) in THF/MeOH/H2O (4/4/4 mL) was stirred for 4 h. The reaction was concentrated under reduced pressure and then water was added to the residue. The aqueous mixture was acidified with 1N HCl to pH˜4. A white precipitate was filtered and washed with water and Et2O. The crude product was dried under vacuum to give compound 11f which was used without purification.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additionwater was added to the residue
  3. filtrationA white precipitate was filtered
  4. washwashed with water and Et2O
  5. dry with materialThe crude product was dried under vacuum

Sources & evidence

ORD record
ord-68b88ad6f557461f9565ab32d7e57796
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

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