Sodium Hydroxide → 5-Bromo-6-methoxybenzo[b]thiophene-3-carboxylic acid

HRID 581982Notes

Reaction equation

HRID 581982 reaction equation
[Br:1][C:2]1[C:15]([O:16][CH3:17])=[CH:14][C:5]2[S:6][CH:7]=[C:8]([C:9]([O:11]CC)=[O:10])[C:4]=2[CH:3]=1.[OH-].[Na+]>C(O)C.O>[Br:1][C:2]1[C:15]([O:16][CH3:17])=[CH:14][C:5]2[S:6][CH:7]=[C:8]([C:9]([OH:11])=[O:10])[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53817228Ethyl 5-bromo-6-methoxybenzo[b]thiophene-3-carboxylate

Product 1

HCID 537810295-Bromo-6-methoxybenzo[b]thiophene-3-carboxylic acidYield 96.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 5-bromo-6-methoxybenzo[b]thiophene-3-carboxylate (D4) (0.42 g, 0.0013 mole) in ethanol (20 ml) and water (5 ml) was treated with sodium hydroxide powder (0.14 g, 0.0035 mole). The reaction mixture was heated under reflux for 2 hours and stirred at ambient temperature for 16 hours. The solvent was removed in vacuo and the residue diluted with water (25 ml), acidified with 5N hydrochloric acid, extracted into ethyl acetate, dried (Na2SO4) and evaporated in vacuo to afford the title compound (0.36 g, 93%) as a beige solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent was removed in vacuo
  4. additionthe residue diluted with water (25 ml)
  5. extractionextracted into ethyl acetate
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-212c164fe6a64f7fbed576362b4b2f64
Source dataset
uspto-grants-1999_07
Patent number
US05922733

Reaction notes

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