Reaktion #676423

Reaktionsgleichung

water

t-BuOK

benzyltriphenylphosphonium bromide

( 62 )

4-(4-bromo-5-(4-methoxyphenyl)thiophen-2-yl)benzaldehyde

→

(E)-3-bromo-2-(4-methoxyphenyl)-5-(4-styrylphenyl)thiophene

Ausbeute 47.0%

Lösungsmittel

THF

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred at RT for 3 h
2. 2
   Extraktionfollowed by extraction with chloroform
3. 3
   TrocknenThe combined extracts were dried over anhydrous MgSO4 and solvent
4. 4
   Sonstigeevaporated to half of its initial volume
5. 5
   Sonstigeby rotary evaporation
6. 6
   Sonstigethe resulting light yellow precipitation
7. 7
   Filtrationwas filtered
8. 8
   Sonstigedried (9.63 g; 47% yield)

Vorschrift

A mixture of benzyltriphenylphosphonium bromide (23.7 g, 54.7 mmol) and (62) (17 g, 45.5 mmol) was dispersed in chloroform (300 mL) and stirred at RT under argon atmosphere for 15 min. A solution of t-BuOK (10.3 g, 91 mmol) in anhydrous THF (80 mL) was added dropwise. The reaction mixture was stirred at RT for 3 h. Then water was added, followed by extraction with chloroform. The combined extracts were dried over anhydrous MgSO4 and solvent evaporated to half of its initial volume by rotary evaporation; the resulting light yellow precipitation was filtered and dried (9.63 g; 47% yield).

Quelle