Hydrochloric Acid → 6-Chloro-1-benzothiophene-2-carboxylic acid

HRID 2243179Notes

Reaction equation

HRID 2243179 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:7]=2[CH:6]=1)=[O:4].[Li+].[OH-].Cl>C1COCC1>[Cl:14][C:11]1[CH:12]=[CH:13][C:7]2[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[S:9][C:8]=2[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 18526200Methyl 6-chloro-1-benzothiophene-2-carboxylate

Product 1

HCID 71419196-Chloro-1-benzothiophene-2-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 630 mg (2.78 mmol) of 6-chloro-benzo[b]thiophene-2-carboxylic acid methyl ester in THF (5 ml) were added 6.95 ml of 1N LiOH-solution and the reaction mixture was stirred at RT for 4 h. The pH was then adjusted to 2-3 by addition of 1N HCl and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to yield 579 mg (98%) of 6-chloro-benzo[b]thiophene-2-carboxylic acid as white solid. MS (ISP) 211.0 (M−H)−.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6e067bc62e794c298c6536800f372422
Source dataset
uspto-grants-2010_03
Patent number
US07674815B2

Reaction notes

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