Réaction #833519

Équation de réaction

hexane

nBuLi

THF

2a

4-bromo-1,2-didecyloxybenzene

→

3,3′,4,4′-tetrakisdecyloxybiphenyl

Rendement 38.0%

Solvants

water

Conditions de réaction

Traitement

1. 1
   Autrehad been precooled to −30° C
2. 2
   workup.ADDITIONOnce the addition
3. 3
   Extractionextracted with ether
4. 4
   LavageThe ether layer was washed with water
5. 5
   Séchagedried with MgSO4
6. 6
   AutreThe solvent was removed under reduced pressure
7. 7
   AutreThe residue was crystallized from a THF/MeOH mixture at −15° C.

Mode opératoire

A hexane solution of nBuLi (1.57 M, 1.02 mL) was added dropwise to a THF solution (50 mL) of 2a which had been precooled to −30° C. Once the addition was complete the reaction mixture was allowed to warm to room temperature. After stirring for an additional 12 h the reaction mixture was poured into water and extracted with ether. The ether layer was washed with water and dried with MgSO4. The solvent was removed under reduced pressure. The residue was crystallized from a THF/MeOH mixture at −15° C. to give colorless crystals of 3,3′,4,4′-tetrakisdecyloxybiphenyl (3a) in 38% yield (mp 85-86° C.).

Source