Methanol → Methyl 4-bromo-5-methylthiophene-2-carboxylate
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
Product 1
Reagents, catalysts & solvents 1
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
- extractionThe aqueous phase was extracted several times with DCM
- dry with materialthe combined organic fractions were dried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a39dc56141e44f86b48dd765c0ed080e
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946278B2
Reaction notes
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