5-(2,2-Dibromoethenyl)-2,2'-bithiophene → 2,2'-Bithiophene, 5-ethynyl-

HRID 1450610Notes

Reaction equation

HRID 1450610 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[S:8][C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:5]=1.[Li]CCCC>C1COCC1>[C:3]([C:4]1[S:8][C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:5]=1)#[CH:2]

Participants

4

Reactant 2

HCID 131139775-(2,2-Dibromoethenyl)-2,2'-bithiopheneHCID 178418339Butyllithium

Product 1

HCID 64520922,2'-Bithiophene, 5-ethynyl-Yield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Anhydrous 5-(2,2-dibromo-ethenyl)-2,2'-bithiophene was dissolved in anhydrous THF and stirred at -78° C. After n-BuLi was added into the solution and stirred for 1 hour, the temperature was raised to 25° C. and stirred for further 1 hour. The solution was monitored by thin layer chromatography to determine whether the reaction was completed. The reaction solution was then extracted with ether and washed with water. After the solution was washed with saturated NaCl solution and dried over anhydrous magnesium sulfate. After removal of ether, the crude product was purified by column chromatography and the oily product was obtained. The yield is 88%.

Workup

  1. stirringstirred for 1 hour
  2. temperaturethe temperature was raised to 25° C.
  3. stirringstirred for further 1 hour
  4. extractionThe reaction solution was then extracted with ether
  5. washwashed with water
  6. washAfter the solution was washed with saturated NaCl solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter removal of ether
  9. customthe crude product was purified by column chromatography
  10. customthe oily product was obtained

Sources & evidence

ORD record
ord-43a70787197c404c81285e26fbdb39e1
Source dataset
uspto-grants-1997_02
Patent number
US05602170

Reaction notes

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