2-Bromo-3-methylthiophene → HCID 10241021, compound

HRID 252261Notes

Reaction equation

HRID 252261 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH3:7].[Mg].[CH2:9](OS(C1C=CC(C)=CC=1)(=O)=O)[CH:10]([CH3:12])[CH3:11]>C(OCC)C>[CH2:9]([C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH3:7])[CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 843142-Bromo-3-methylthiopheneHCID 3105902-Methylpropyl 4-methylbenzene-1-sulfonateHCID 5462224Magnesium

Product 1

HCID 10241021HCID 10241021, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A part of a solution containing 2-bromo-3-methylthiophene (1.5 g, 8.5 mmol) in dry diethyl ether is added drop-wise to a suspension of magnesium (308 mg, 12.7 mmol, 1.5 equiv.) in dry diethyl ether until the mixture starts to reflux. The remaining solution is added dropwise. A solution of toluene-4-sulfonic acid isobutyl ester (2.9 g, 12.7 mmol, 1.5 equiv.) in dry diethyl ether is added dropwise at room temp., then the mixture is further refluxed for two hours. After cooling to room temp., the mixture is quenched with sat. ammonium chloride solution and extracted with tert. butylmethylether. The combined organic extracts are washed with water, brine, dried over magnesiumsulfat-dihydrate, filtered and evaporated to give a yellow oil. After Kugelrohr-distillation, 630 mg of the title compound is obtained as a colorless oil. GC-MS (EI): M=154

Workup

  1. additionis added drop-wise
  2. temperatureto reflux
  3. additionThe remaining solution is added dropwise
  4. temperaturethe mixture is further refluxed for two hours
  5. temperatureAfter cooling to room temp.
  6. customthe mixture is quenched with sat. ammonium chloride solution
  7. extractionextracted with tert. butylmethylether
  8. washThe combined organic extracts are washed with water, brine
  9. dry with materialdried over magnesiumsulfat-dihydrate
  10. filtrationfiltered
  11. customevaporated
  12. customto give a yellow oil
  13. distillationAfter Kugelrohr-distillation

Sources & evidence

ORD record
ord-d9295be04517405aa91c4ff1746a84e0
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Reaction notes

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