Reacción #976966

Ecuación de reacción

10-bromobenzo[g]chrysene

ether

ether

triisopropyl borate

hydrochloric acid

n-butyllithium hexane

→

benzo[g]chrysene-10-boronic acid

Rendimiento 60.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas placed in a flask
2. 2
   TemperaturaAfter heating to 0° C.
3. 3
   TemperaturaThe reaction solution was cooled to −60° C.
4. 4
   workup.ADDITIONwas added
5. 5
   workup.STIRRINGThe reaction solution was stirred for 5 hours
6. 6
   Temperaturawith heating to room temperature
7. 7
   workup.STIRRINGstirring
8. 8
   workup.WAITwas conducted for 1 hour
9. 9
   OtroAn aqueous phase was removed
10. 10
    Otroan organic phase which had been separated
11. 11
    Lavadowas washed with water and saturated brine
12. 12
    Secadodried with magnesium sulfate
13. 13
    FiltraciónAfter the magnesium sulfate was filtered out
14. 14
    Concentraciónthe organic phase was concentrated
15. 15
    LavadoThe resulting solids were washed with hexane

Procedimiento

Under an argon atmosphere, 5.87 g of 10-bromobenzo[g]chrysene which had been prepared in Synthesis Example 2 was placed in a flask and 100 mL of dehydrated ether was added to this flask. The reaction solution was cooled to −40° C. and 11 ml of 1.6M n-butyllithium hexane solution was added. After heating to 0° C., the resultant was stirred for 1 hour. The reaction solution was cooled to −60° C. and 10 mL of dehydrated ether solution in which 7.72 g of triisopropyl borate was dissolved was added. The reaction solution was stirred for 5 hours with heating to room temperature. 50 mL of 10% aqueous solution of hydrochloric acid was added and stirring was conducted for 1 hour. An aqueous phase was removed and an organic phase which had been separated was washed with water and saturated brine, and then dried with magnesium sulfate. After the magnesium sulfate was filtered out, the organic phase was concentrated. The resulting solids were washed with hexane, whereby 3.18 g (yield: 60%) of benzo[g]chrysene-10-boronic acid was obtained.

Fuente