Sulfur Dioxide → 5-Methyl-thiophene-3-sulfonic acid lithium salt

HRID 1009025Notes

Reaction equation

HRID 1009025 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:7])[S:5][CH:6]=1.C([Li:12])(C)(C)C.[S:13](=[O:15])=[O:14].C([O:18]CC)C>CCCCC>[Li+:12].[CH3:7][C:4]1[S:5][CH:6]=[C:2]([S:13]([O-:18])(=[O:15])=[O:14])[CH:3]=1

Participants

6

Reactant 4

HCID 1119Sulfur DioxideHCID 3283Diethyl EtherHCID 6385844-Bromo-2-methylthiopheneHCID 178418306HCID 178418306, compound

Product 1

HCID 873485635-Methyl-thiophene-3-sulfonic acid lithium salt

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To a solution of 4-bromo-2-methyl-thiophene (1.594 g, 9.00 mmol) in 5.0 mL of diethyl ether was added dropwise 2.1 mL of tert-butyllithium in pentane (1.7 M, 09 eq.). After stirring for 20 Min. at −78° C., sulfur dioxide (condensed, ca. 4 mL) was added dropwise and the reaction mixture kept for another 30 min at this temperature. The dry ice cooling bath was removed and the reaction mixture diluted with heptane; the precipitated solid was collected, washed with some heptane and dried at high vacuum to yield 1.100 g of the title compound as white solid.

Workup

  1. customThe dry ice cooling bath was removed
  2. additionthe reaction mixture diluted with heptane
  3. customthe precipitated solid was collected
  4. washwashed with some heptane
  5. customdried at high vacuum

Sources & evidence

ORD record
ord-8be25c37bbde44d59aa858eaa76645b9
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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