Reaktion #216981

Reaktionsgleichung

1-bromo-4-butylbenzene

t-butyllithium

4-iodobenzenepropanoic acid, ethyl ester

→

title compound

Ausbeute 91.0%

4'-Butyl[1,1'-biphenyl]-4-propanoic acid, ethyl ester

Ausbeute 91.0%

Lösungsmittel

THF

ether

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe resulting slurry was stirred for 30 min
2. 2
   workup.STIRRINGThe reaction was stirred for 16 h
3. 3
   Waschenwashed once with 10% citric acid
4. 4
   TrocknenThe organic phase was dried (MgSO4)
5. 5
   Sonstigeevaporated
6. 6
   SonstigePurification by flash chromatography on silica gel (5×20 cm column)
7. 7
   Wascheneluted with 1:1 hexanes/dichloromethane

Vorschrift

To a stirred solution of 3.20 g (15.0 mmol) of 1-bromo-4-butylbenzene (Aldrich Chemical Company #33,576-2) at -78° C. under argon was added, dropwise over 30 min, 18.0 mL (30.6 mmol, 1.7M in pentane) of t-butyllithium solution. The resulting light yellow solution was warmed to 0° C. and stirred for 1 h. To this solution was added 3.4 g (25 mmol) of thrice-fused zinc chloride in 20 mL of THF. The resulting slurry was stirred for 30 min and then a solution of 2.0 g (6.5 mmol) of 4-iodobenzenepropanoic acid, ethyl ester (Example 43, Part B) and 0.4 g (0.35 mmol) of tetrakis(triphenylphosphine)palladium (0) in 5 mL of THF was added. The reaction was stirred for 16 h, diluted with ether and washed once with 10% citric acid. The organic phase was dried (MgSO4) and evaporated. Purification by flash chromatography on silica gel (5×20 cm column) eluted with 1:1 hexanes/dichloromethane gave title compound as a colorless oil, 1.79 g , 91% yield.

Quelle