Reaktion #70284

Reaktionsgleichung

1,3-difluoro-5-methoxybenzene

n-BuLi

5-bromo-2-iodopyrimidine

→

5-Bromo-2-(2,6-difluoro-4-methoxyphenyl)pyrimidine

Lösungsmittel

THF

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturit was heated to −50° C
2. 2
   workup.STIRRINGthe mixture was stirred at this temperature for 20 minutes
3. 3
   SonstigeThe solvent was evaporated
4. 4
   Sonstigethe crude mixture was purified over SiO2 eluting with mixtures of hexane/ethyl acetate affording 0.89 g (39% of yield) of the expected product

Vorschrift

In a three neck round bottle flask, to a mixture of 1,3-difluoro-5-methoxybenzene (8.39 mmol, 0.98 ml) in THF (40 ml) at −78° C. under argon atmosphere, a solution of n-BuLi (9.13 mmol, 3.65 ml) in THF (2.5M) was added. The mixture was stirred at −78° C. for 30 minutes and then it was heated to −50° C. A solution of ZnCl2 (9.13 mmol, 18.3 ml) in THF (0.5M) was added dropwise and the mixture was stirred at this temperature for 20 minutes. A solution of 5-bromo-2-iodopyrimidine (7.02 mmol, 2.0 g) in THF (5 ml) and Pd(PPh3)4 (0.70 mmol, 0.81 g) were added respectively and the crude mixture was heated at 40° C. overnight. The solvent was evaporated and the crude mixture was purified over SiO2 eluting with mixtures of hexane/ethyl acetate affording 0.89 g (39% of yield) of the expected product.

Quelle