Reacción #1069768

Ecuación de reacción

triisopropyl borate

ether

1-Bromopyrene

n-Butyllithium

→

pyreneboronic acid

Disolventes

water

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITThis mixture was kept at −78° C. for ten minutes, 0° C. for ten minutes
2. 2
   workup.WAIT−78° C. for thirty minutes
3. 3
   workup.WAITthe mixture was kept at −78° C. for thirty minutes
4. 4
   OtroFinally, the mixture underwent reaction at room temperature for 1.5 days
5. 5
   OtroThe water layer and the organic layer were separated
6. 6
   Extracciónthe water layer was then extracted by ethyl ether (2×25 ml)
7. 7
   Lavadowashed (2×50 ml)
8. 8
   Otroto remove water
9. 9
   Filtraciónfiltered
10. 10
    Concentraciónconcentrated on a rotary evaporator

Procedimiento

1-Bromopyrene (2.00 g, 7.12 mmol) was dissolved in anhydrous THF (150 ml) and anhydrous ether (150 ml). The light yellow solution was cooled to −78° C. in nitrogen. n-Butyllithium (4.9 ml, 7.83 mmol) was slowly dripped into the solution. At this time, the solution became murky. This mixture was kept at −78° C. for ten minutes, 0° C. for ten minutes, and then −78° C. for thirty minutes. Then, triisopropyl borate (4.93 ml, 21.36 mmol) was slowly dripped into the solution, and the mixture was kept at −78° C. for thirty minutes. Finally, the mixture underwent reaction at room temperature for 1.5 days. Next, water was added into the reaction mixture, and the resulting mixture was stirred vigorously for one hour. The water layer and the organic layer were separated, the water layer was then extracted by ethyl ether (2×25 ml), and the organic layer was water washed (2×50 ml). The combined organic solution was contact with MgSO4 to remove water, then filtered, and concentrated on a rotary evaporator to obtain a pyreneboronic acid solid product.

Fuente