Styrene → trans-Stilbene

HRID 1825707Notes

Reaction equation

HRID 1825707 reaction equation
C(N(CCCC)CCCC)CCC.[CH2:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[C:16]1(/[CH:15]=[CH:14]/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 7501StyreneHCID 7622TributylamineHCID 7964Chlorobenzene

Product 1

HCID 638088trans-Stilbene

Procedure

In a 100 mL Schlenk flask, the NAIL (3.23 g, 10 mmol)(NBu4Br) was heated to melt (130° C.) and degassed with nitrogen and vacuum prior to the addition of other reagents. After cooling the NAIL to room temperature, LDH-Pd0 (3 mol %), tri-n-butyl amine (222 mg, 1.2 mmol) were added. The styrene (1.2 mmol) and chlorobenzene (1 mmol) were then added and the reaction was heated to 130° C. and stirred for 10–40 h under nitrogen atmosphere, After completion of the reaction, the LDH-Pd0 catalyst was filtered and washed with water and dichloromethane. After removing the solvent, the crude material was chromatographed on silica gel or recrystallized from ethanol to afford the trans-stilbene.

Workup

  1. temperatureIn a 100 mL Schlenk flask, the NAIL (3.23 g, 10 mmol)(NBu4Br) was heated
  2. custom(130° C.)
  3. customdegassed with nitrogen and vacuum
  4. additionto the addition of other reagents
  5. temperaturethe reaction was heated to 130° C.
  6. customAfter completion of the reaction
  7. filtrationthe LDH-Pd0 catalyst was filtered
  8. washwashed with water and dichloromethane
  9. customAfter removing the solvent
  10. customthe crude material was chromatographed on silica gel
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6cd84b210dc54573bada0581dba88273
Source dataset
uspto-grants-2006_05
Patent number
US07049266B2

Reaction notes

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