Methyl 3-bromothiophene-2-carboxylate → 3-Bromothiophene-2-carboxylic acid

HRID 357739

Reaction equation

HRID 357739 reaction equation
C[O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[Br:10])=[O:4]>CO.O1CCCC1.[OH-].[Na+]>[Br:10][C:9]1[CH:8]=[CH:7][S:6][C:5]=1[C:3]([OH:4])=[O:2]

Participants

5

Reactant 1

HCID 2740074Methyl 3-bromothiophene-2-carboxylate

Product 1

HCID 27396883-Bromothiophene-2-carboxylic acidYield 97.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

3-Bromo-2-thiophenecarboxylic acid methyl ester (7.74 g) was dissolved in a mixture of methanol (35 ml) and tetrahydrofuran (35 ml), and 1N aqueous sodium hydroxide (53 ml) was added. The mixture was stirred at room temperature for 2 hours and washed with diethyl ether. The aqueous layer was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 3-bromo-2-thiophenecarboxylic acid (7.05 g) as crystals.

Workup

  1. additionwas added
  2. washwashed with diethyl ether
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2e768a02cf3442ff911f2d68e5377a5c
Source dataset
uspto-grants-1998_11
Patent number
US05840917

Linked notes

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