Reaktion #688629

Reaktionsgleichung

n-Butyllithium

p-n-octyliodobenzene

HCl

trimethylborate

→

p-n-octylphenylboronic acid

Ausbeute 84.1%

Lösungsmittel

THF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITto return to room temperature after 1 hour
2. 2
   workup.WAITwas left
3. 3
   workup.STIRRINGstirring under nitrogen overnight
4. 4
   workup.STIRRINGstirring
5. 5
   workup.WAITwas continued for 2 hours
6. 6
   ExtraktionThe mixture was extracted with ether (15 3 mL)
7. 7
   Waschenwas washed with brine and water (20 2 mL)
8. 8
   Trocknendried with MgSO4
9. 9
   Sonstigethe solvent removed in vacuo

Vorschrift

n-Butyllithium (BuLi, 1.6 M in hexanes, 2.4 mL, 3.8 mmol) was added dropwise to a stirred solution of p-n-octyliodobenzene (1.0 g, 3.2 mmol) in dry THF (15 mL) at −78° C. under nitrogen. After stirring for 30 minutes and maintaining the temperature at −78° C., trimethylborate (0.4 g, 3.8 mmol) was added dropwise. The system was allowed to return to room temperature after 1 hour and was left stirring under nitrogen overnight. Concentrated HCl (8 mL) and water (15 mL) were then added and stirring was continued for 2 hours. The mixture was extracted with ether (15 3 mL). The ethereal phase was combined and was washed with brine and water (20 2 mL), dried with MgSO4, and the solvent removed in vacuo to give p-n-octylphenylboronic acid as a white solid (0.63 g, 84% yield).

Quelle