Methanol → Methyl 4-bromothiophene-2-carboxylate

HRID 1961154Notes

Reaction equation

HRID 1961154 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.[CH3:15]O>>[Br:1][C:2]1[CH:3]=[C:4]([C:7]([O:9][CH3:15])=[O:8])[S:5][CH:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 6104094-Bromo-2-thiophenecarboxylic Acid

Product 1

HCID 12752071Methyl 4-bromothiophene-2-carboxylateYield 97%

Conditions

Temperature
50 °C

Procedure

To a solution of 4-bromo-2-thiophenecarboxylic acid (25 g, 121 mmol) in methanol (241 ml) was added sulfuric acid (32 ml, 604 mmol). The resulting solution stirred at 50° C. over 4 d. The solution was partitioned between H2O-DCM and the aqueous phase was washed several times with DCM. The combined organic fractions were dried over Na2SO4, concentrated and used directly without further purification providing methyl 4-bromo-2-thiophenecarboxylate (26 g, 118 mmol, 97% yield), LCMS (ES) m/e 222 (M+H)+.

Workup

  1. customThe solution was partitioned between H2O-DCM
  2. washthe aqueous phase was washed several times with DCM
  3. dry with materialThe combined organic fractions were dried over Na2SO4
  4. concentrationconcentrated
  5. customused directly without further purification

Sources & evidence

ORD record
ord-3ae402330cfe41308e34479618ffe16e
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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