Reaktion #733828

Reaktionsgleichung

sec-BuLi

9-bromoanthracene

HCl

Triisopropylborate

→

9-anthraceneboronic acid

Ausbeute 94.6%

Lösungsmittel

Et2O

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction was stirred at rt for 18 h
2. 2
   workup.STIRRINGthe reaction was stirred for 30 minutes
3. 3
   SonstigeThe layers were separated
4. 4
   Extraktionthe aqueous phase was extracted three times with CH2Cl2
5. 5
   WaschenThe combined organic layers were washed with H2O, sat. NaHCO3 (aq.), brine
6. 6
   Trocknendried over Na2SO4
7. 7
   FiltrationFiltration and concentration

Vorschrift

sec-BuLi (4.3 mL, 6.0 mmol, 1.4M solution in cyclohexane) was added dropwise to a solution of 9-bromoanthracene (1.29 g, 5.0 mmol) in Et2O (20 mL) at 0° C. under N2. The reaction was held at 0° C. for 15 minutes then warmed to rt and stirred an additional 45 minutes. Triisopropylborate (1.5 mL, 6.5 mmol) was added and the reaction was stirred at rt for 18 h. Concentrated HCl (1.0 mL) and MeOH (1.0 mL) was added and the reaction was stirred for 30 minutes. The layers were separated and the aqueous phase was extracted three times with CH2Cl2. The combined organic layers were washed with H2O, sat. NaHCO3 (aq.), brine, and then dried over Na2SO4. Filtration and concentration gave 1.05 g of 9-anthraceneboronic acid.

Quelle