Sodium Hydroxide → HCID 178435087, compound

HRID 2298690Notes

Reaction equation

HRID 2298690 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10]C)=[S:9])[S:5][C:6]=1[CH3:7].[OH-].[Na+]>CO.O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([OH:10])=[S:9])[S:5][C:6]=1[CH3:7]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86583861Methyl 4-bromo-5-methylthiothiophene-2-carboxylate

Product 1

HCID 178435087HCID 178435087, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 1.0 g (3.7 mmol) of methyl 4-bromo-5-methylthiothiophene-2-carboxylate (as prepared in Example 241, step (a) dissolved in 25 ml of MeOH was added 450 mg of NaOH dissolved in 10 ml of H2O. The reaction was stirred for 5 hours at room temperature, and then the solvents were removed under vacuum. The residue of the reaction was extracted with ethyl acetate (2×50 mL) and 1N HCl. The organic layer was collected, dried (Na2SO4), filtered and concentrated under vacuum to yield 833 mg (89%) of 4-bromo-5-methylthiothiophene-2-carboxylic acid as a white solid.

Workup

  1. customthe solvents were removed under vacuum
  2. extractionThe residue of the reaction was extracted with ethyl acetate (2×50 mL) and 1N HCl
  3. customThe organic layer was collected
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cfb4b2fe0a3e4295bf63c692cff55db8
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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