Thiophenol → 2-(Phenylthio)thiophene

HRID 467136Notes

Reaction equation

HRID 467136 reaction equation
ClN1C(=O)CCC1=O.[C:9]1([SH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[Li].C([Li])CCC.S1C=CC=C1>C1C=CC=CC=1.O1CCCC1>[C:9]1([S:15][C:17]2[S:16][CH:20]=[CH:19][CH:18]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

8

Reactant 5

HCID 7969ThiophenolHCID 8030ThiopheneHCID 31398ChlorosuccinimideHCID 178418339ButyllithiumHCID 178418439HCID 178418439, compound

Product 1

HCID 27789152-(Phenylthio)thiophene

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-15 °C

Procedure

To a suspension of N-chlorosuccinimide (7.8 g) in benzene (30 ml) was added dropwise, a solution of thiophenol (5.51 g) in benzene (20 ml) at room temperature. After 1 hour, the suspension was filtered, the filter pad washed with benzene and the filtrate evaporated under reduced pressure to give an orange oil. The oil was dissolved in dry tetrahydrofuran (20 ml) and added dropwise to a solution of 2-thienyl-lithium (prepared by the addition of n-butyllithium (20 ml, 2.5M) to thiophene (4.2 g) in dry tetrahydrofuran (30 ml) at -15° C. under nitrogen and stirred for 2 hours) at -15° C. under N2. The solution was stirred for 1 hour, allowed to warm to room temperature and stirred overnight. The reaction mixture was poured on to ice, extracted with ether (3×100 ml), dried over MgSO4 and evaporated under reduced pressure to give a brown oil. The oil was flash chromatographed on a Sorbsil C60-40/60H column using petroleum ether (40°-60° C.) to give a colourless oil, b.p. 161° C./20 mm pressure.

Workup

  1. additionwas added dropwise
  2. customat room temperature
  3. filtrationthe suspension was filtered
  4. washthe filter pad washed with benzene
  5. customthe filtrate evaporated under reduced pressure
  6. customto give an orange oil
  7. stirringThe solution was stirred for 1 hour
  8. temperatureto warm to room temperature
  9. stirringstirred overnight
  10. additionThe reaction mixture was poured on to ice
  11. extractionextracted with ether (3×100 ml)
  12. dry with materialdried over MgSO4
  13. customevaporated under reduced pressure
  14. customto give a brown oil
  15. customchromatographed on a Sorbsil
  16. custompetroleum ether (40°-60° C.)
  17. customto give a colourless oil, b.p. 161° C./20 mm pressure

Sources & evidence

ORD record
ord-c351123020024690a3ebc4e0d69322dc
Source dataset
uspto-grants-1992_10
Patent number
US05158971

Reaction notes

Loading…