Methanol → Methyl 4-bromo-5-methylthiophene-2-carboxylate

HRID 2391951Notes

Reaction equation

HRID 2391951 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([OH:10])=[O:9])[S:5][C:6]=1[CH3:7].[CH3:11]O>OS(O)(=O)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[S:5][C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 887MethanolHCID 8188894-Bromo-5-methylthiophene-2-carboxylic acid

Product 1

HCID 18536848Methyl 4-bromo-5-methylthiophene-2-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 4-bromo-5-methyl-2-thiophenecarboxylic acid (3 g, 13.6 mmol) in MeOH (67 mL) and H2SO4 (3 mL) was stirred at 50° C. After 12 h, the solution was added to ice-H2O and the pH was adjusted to ˜11. The aqueous phase was extracted several times with DCM and the combined organic fractions were dried over Na2SO4, concentrated and used directly yielding the title compound (3 g, 94%) as an orange solid: LCMS (ES) m/z 236 (M+H)+.

Workup

  1. extractionThe aqueous phase was extracted several times with DCM
  2. dry with materialthe combined organic fractions were dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-72fb4a3f407a46a396fdc4b107fa07c4
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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