Methyl iodide → Methyl 4-bromo-3-methoxythiophene-2-carboxylate

HRID 551292Notes

Reaction equation

HRID 551292 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[C:8]([Br:11])[C:9]=1[OH:10])=[O:4].[C:12](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[C:8]([Br:11])[C:9]=1[O:10][CH3:12])=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2777611Methyl 4-bromo-3-hydroxythiophene-2-carboxylate

Product 1

HCID 2736824Methyl 4-bromo-3-methoxythiophene-2-carboxylateYield 129.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl-3-hydroxy-4-bromo-2-thiophenecarboxylate (10.0 g, 42.2 mmol) was dissolved in 250 mL of acetone. Potassium carbonate (30.0 g, 217.4 mmol) was added followed by a solution of iodomethane (14.5 mL, 233.0 mmol). The mixture was heated to reflux and continued for 6 h. After cooled to room temperature, the mixture was filtered, the solid material was rinsed with acetone (˜200 mL). The filtrate and rinsing were concentrated under reduced pressure to a solid, further dried on high vacuum, yielding 13.7 g (100%) of methyl-3-methoxy-4-bromo-2-thiophenecarboxylate (MH+=251.0).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. filtrationthe mixture was filtered
  4. washthe solid material was rinsed with acetone (˜200 mL)
  5. washThe filtrate and rinsing
  6. concentrationwere concentrated under reduced pressure to a solid
  7. customfurther dried on high vacuum

Sources & evidence

ORD record
ord-f3a08a532b2a4c9eb461555af5189dad
Source dataset
uspto-grants-2011_05
Patent number
US07947720B2

Reaction notes

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