Methanol → Methyl 5-bromothiophene-2-carboxylate

HRID 2235254Notes

Reaction equation

HRID 2235254 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[OH-].[Na+].[CH3:17]O>CCOC(C)=O.O>[CH3:17][O:8][C:7]([C:5]1[S:6][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:9]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 3491155-Bromothiophene-2-carboxylic acid

Product 1

HCID 605713Methyl 5-bromothiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

To a solution of 5-bromo-thiophene-2-carboxylic acid (1.04 g, 5.0 mmol) in 15 mL of methanol, add concentrated sulfuric acid (0.5 ml, 10 mmol). After heating to reflux for an hour, cool the reaction to room temp, and dilute with EtOAc/H2O=50/50. Then, neutralize with 1.0 N NaOH to pH=7, extract the aqueous solution with ethyl acetate (30 ml×3), and dry the combined organic layers over sodium sulfate. Purify the crude material via flash chromatograpgy on sila gel to give the title compound 0.62 g. GC/MS (m/z) 222 (M+1), 191 (M—OMe+1).

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for an hour
  3. temperaturecool
  4. customthe reaction to room temp
  5. extractionextract the aqueous solution with ethyl acetate (30 ml×3)
  6. dry with materialdry the combined organic layers over sodium sulfate
  7. customPurify the crude material via flash chromatograpgy on sila gel

Sources & evidence

ORD record
ord-7a36f9a348cd4f31bae3a19f8081afa8
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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