Reacción #2005

Ecuación de reacción

water

2-propanol

4-tolylboronic acid

2-bromo-1-nitrobenzene

→

product

Rendimiento 77.4%

4-Methyl-2'-nitro-1,1'-biphenyl

Rendimiento 77.4%

Disolventes

sodium hydroxide

benzene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe two-phase mixture was heated
2. 2
   Temperaturaat reflux for three hours
3. 3
   OtroThe cooled reaction mixture
4. 4
   Filtraciónwas filtered through Celite
5. 5
   Lavadothe filter cake washed with fresh benzene
6. 6
   OtroThe organic layer was separated
7. 7
   Lavadowashed with water (3×)
8. 8
   Secadodried over magnesium sulfate
9. 9
   Filtraciónfiltered
10. 10
    OtroThe filtrate was evaporated under vacuum
11. 11
    Otrothe residue (46.1 g) purified by preparative high pressure liquid chromatography on silica gel
12. 12
    Lavadoeluting with hexane/ethyl acetate (20:1)

Procedimiento

A vigorously stirred mixture of 34 g (0.25 mol) of 4-tolylboronic acid and 34 g (0.17 mol) of 2-bromo-1-nitrobenzene in a mixture of 170 mL of 5N sodium hydroxide, 57 mL of water, 215 mL of 2-propanol and 1080 mL of benzene was treated with 11.9 g of (tetrakis)triphenylphosphine palladium(0). The two-phase mixture was heated at reflux for three hours. The cooled reaction mixture was filtered through Celite and the filter cake washed with fresh benzene. The organic layer was separated and washed with water (3×), dried over magnesium sulfate and filtered. The filtrate was evaporated under vacuum and the residue (46.1 g) purified by preparative high pressure liquid chromatography on silica gel, eluting with hexane/ethyl acetate (20:1), to give 28.05 g of the product.

Fuente