Reaktion #52977

Reaktionsgleichung

(MeO)3B

LDA

1,3-Dicyanobenzene

Water

→

2,6-dicyanobenzeneboronic acid

Lösungsmittel

HOAc

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature
2. 2
   workup.STIRRINGstirred overnight
3. 3
   workup.STIRRINGthe resulting mixture was stirred for 0.5 h
4. 4
   Extraktionextracted with EtOAc
5. 5
   WaschenThe organic layer was further washed with water and brine
6. 6
   Trocknendried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated
9. 9
   Filtrationfiltered
10. 10
    Sonstigeevaporated

Vorschrift

1,3-Dicyanobenzene (1.00 g) was dissolved in freshly distilled THF (70 mL). This solution was cooled to −96° C. and LDA (4.2 mL of a 2M solution) was added dropwise to the cold solution under N2. The mixture was stirred for 30 min at −96° C. and (MeO)3B (1.3 mL) was added. The resulting mixture was allowed to warm to room temperature and stirred overnight. Water was added and the resulting mixture was stirred for 0.5 h, then acidified with HOAc and extracted with EtOAc. The organic layer was further washed with water and brine, dried (MgSO4), filtered and evaporated. The residue was taken up in CH2Cl2, filtered and evaporated to yield 2,6-dicyanobenzeneboronic acid (0.56 g).

Quelle