Reaktion #52908

Reaktionsgleichung

Water

n-BuLi

1,3-Dimethoxybenzene

(MeO)3B

→

2,6-dimethoxybenzeneboronic acid

Lösungsmittel

acetic acid

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwarmed to room temperature
2. 2
   workup.STIRRINGstirred for 1 h
3. 3
   TemperaturThe resulting mixture was cooled again to −78° C.
4. 4
   Temperaturto warm to room temperature
5. 5
   workup.STIRRINGstirred overnight
6. 6
   workup.STIRRINGthe mixture was stirred for 0.5 h
7. 7
   Extraktionextracted with EtOAc
8. 8
   TrocknenThe extract was dried (MgSO4)
9. 9
   Sonstigeevaporated

Vorschrift

1,3-Dimethoxybenzene (4 g) was dissolved in freshly distilled THF (10 mL). This solution was cooled to −78° C. and n-BuLi (24 mL, 1.6 M solution in hexanes) was added dropwise to the cold solution. The mixture was stirred at −78° C. for 1 h, then warmed to room temperature and stirred for 1 h. The resulting mixture was cooled again to −78° C. and (MeO)3B (6.7 mL) was added. The mixture was allowed to warm to room temperature and stirred overnight. Water (10 mL) was added, and the mixture was stirred for 0.5 h, acidified to pH 4 with acetic acid and extracted with EtOAc. The extract was dried (MgSO4) and evaporated to give 2,6-dimethoxybenzeneboronic acid, which was used without further purification.

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