Sulfur Dioxide → Lithium 4-methyl-3-thiophenesulfinate

HRID 1248378Notes

Reaction equation

HRID 1248378 reaction equation
Br[C:2]1[C:6]([CH3:7])=[CH:5][S:4][CH:3]=1.C([Li:12])CCC.[S:13](=[O:15])=[O:14]>C(OCC)C.CCCCCC>[CH3:7][C:6]1[C:2]([S:13]([O-:15])=[O:14])=[CH:3][S:4][CH:5]=1.[Li+:12]

Participants

6

Reactant 3

HCID 1119Sulfur DioxideHCID 27349353-Bromo-4-methylthiopheneHCID 178418339Butyllithium

Product 1

HCID 23669555Lithium 4-methyl-3-thiophenesulfinate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

To 30 g of 3-bromo-4-methylthiophene in 150 ml of anhydrous ethyl ether under nitrogen at -70° to -75° C. was added, cautiously, during 30 minutes 111 ml of 1.6M butyl lithium in hexane. The mixture was stirred for an additional thirty minutes and then 30 ml of liquified sulfur dioxide was added at such a rate that the temperature of the reaction mixture was maintained below -70° C. Upon completion of the addition, the mixture was stirred for an additional 90 minutes at -75° C. and then allowed to stand overnight at room temperature. The resulting precipitate was filtered and washed with ethyl ether, dried in air and in vacuo under nitrogen to yield 30 g of the desired salt, m.p. >250° C.

Workup

  1. temperaturewas maintained below -70° C
  2. additionUpon completion of the addition
  3. stirringthe mixture was stirred for an additional 90 minutes at -75° C.
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with ethyl ether
  6. customdried in air and in vacuo under nitrogen

Sources & evidence

ORD record
ord-9c83418814a64a63b686491b5acf7391
Source dataset
uspto-grants-1985_06
Patent number
US04523943

Reaction notes

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