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

HRID 217436Notes

Reaction equation

HRID 217436 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([OH:11])=[O:10])[S:5][C:6]=1[CH2:7][CH3:8].O=S(Cl)Cl.[CH3:16]O>>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([O:11][CH3:16])=[O:10])[S:5][C:6]=1[CH2:7][CH3:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 37663724-Bromo-5-ethylthiophene-2-carboxylic acid

Product 1

HCID 57826917Methyl 4-bromo-5-ethylthiophene-2-carboxylate

Conditions

Temperature
0 °C

Procedure

The suspension of 4-bromo-5-ethylthiophene-2-carboxylic acid (800 mg) in MeOH (4 mL) was added dropwise SOCl2 (0.50 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour, warmed to 60° C., and then stirred for 15 hours. The reaction liquid was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=98:2 to 70:30) to obtain methyl 4-bromo-5-ethylthiophene-2-carboxylate (765.0 mg) as a colorless liquid.

Workup

  1. temperaturewarmed to 60° C.
  2. stirringstirred for 15 hours
  3. customThe reaction liquid
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=98:2 to 70:30)

Sources & evidence

ORD record
ord-22af2f5622c6457db064bd64a56613b4
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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