Sodium Hydroxide → 2-Bromo-5-phenylthiophene-3-carboxylic acid

HRID 590991Notes

Reaction equation

HRID 590991 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][C:6]=1[C:7]([O:9]C)=[O:8].[OH-].[Na+]>C(O)C.O>[Br:1][C:2]1[S:3][C:4]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70818321Methyl 2-bromo-5-phenylthiophene-3-carboxylate

Product 1

HCID 581103102-Bromo-5-phenylthiophene-3-carboxylic acidYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 2-bromo-5-phenylthiophene-3-carboxylate (11c) (290 mg, 0.97 mmol) and sodium hydroxide (156 mg, 3.90 mmol) in a mixture of ethanol (6 mL) and water (2 mL) was refluxed for 30 minutes. The mixture was concentrated in vacuo. The remained aqueous layer was washed with diethyl ether (5 mL), acidified with 1N hydrochloric acid until pH 3 and was extracted with dichloromethane (2×10 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to provide the desired acid (11d) (260 mg, 0.92 mmol, 95%), which was used without further purification.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. concentrationThe mixture was concentrated in vacuo
  3. washThe remained aqueous layer was washed with diethyl ether (5 mL)
  4. extractionwas extracted with dichloromethane (2×10 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-735c9d9aa1e643a28b3df0ee1d37425a
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

Loading…