Ethanol → Ethyl 4-bromothiophene-2-carboxylate

HRID 1036986Notes

Reaction equation

HRID 1036986 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:7]([OH:9])=[O:8])[S:5][CH:6]=1.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[CH2:20](O)[CH3:21]>O>[Br:1][C:2]1[CH:3]=[C:4]([C:7]([O:9][CH2:20][CH3:21])=[O:8])[S:5][CH:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 6104094-Bromo-2-thiophenecarboxylic Acid

Product 1

HCID 10847330Ethyl 4-bromothiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

663 mg (3.20 mmol) of the compound from Example 6A are provided in 25 ml of ethanol, 0.1 ml of concentrated sulfuric acid is added and the mixture is heated under reflux overnight. After cooling to room temperature, a saturated aqueous sodium bicarbonate solution is added and the mixture is diluted with water and extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated. 700 mg (89% of theory) of the title compound are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux overnight
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-96a238aeec2a4734962534341646e20c
Source dataset
uspto-grants-2013_10
Patent number
US08546438B2

Reaction notes

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