Hydrochloric Acid → 5-Bromothiophene-3-carboxylic acid

HRID 1864533Notes

Reaction equation

HRID 1864533 reaction equation
[OH-].[Na+].[Br:3][C:4]1[S:8][CH:7]=[C:6]([C:9]([O:11]CC)=[O:10])[CH:5]=1.Cl>O1CCCC1.CO.O.C(OCC)(=O)C>[Br:3][C:4]1[S:8][CH:7]=[C:6]([C:9]([OH:11])=[O:10])[CH:5]=1

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15293216Ethyl 5-bromothiophene-3-carboxylate

Product 1

HCID 120399785-Bromothiophene-3-carboxylic acidYield 92%

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

7.4 g (185 mmol) of sodium hydroxide pellets are added to a solution of 8.7 g (37 mmol) of ethyl 5-bromothiophene-3-carboxylate in 100 ml of tetrahydrofuran, 10 ml of methanol and a few drops of water. After stirring at room temperature for 18 hours, the reaction medium is taken up in ethyl acetate and washed with water. The aqueous phase obtained is acidified to pH 1 with aqueous hydrochloric acid solution and then extracted with dichloromethane. The organic phase obtained is dried over magnesium sulfate, filtered and concentrated under vacuum. 7 g (92%) of 5-bromothiophene-3-carboxylic acid are obtained.

Workup

  1. washwashed with water
  2. customThe aqueous phase obtained
  3. extractionextracted with dichloromethane
  4. customThe organic phase obtained
  5. dry with materialis dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a566a6e028174c5d81876df10d99b9dd
Source dataset
uspto-grants-2009_12
Patent number
US07625914B2

Reaction notes

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