Reacción #65893

Ecuación de reacción

4-methylphenyl boronic acid

sodium carbonate

water

Compound C

5-(2-bromophenyl)-1-(4-nitrophenyl)-1H-tetrazole

→

5-(4'-methylbiphenyl-2-yl)-1-(4-nitrophenyl)-1H-tetrazole

Rendimiento 95.1%

Disolventes

toluene

methanol

Toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto give a clear solution
2. 2
   Temperaturathe mixture heated
3. 3
   Temperaturaat reflux for 3 hours
4. 4
   Filtraciónthe warm mixture was filtered through diatomaceous earth
5. 5
   OtroThe organic phase was separated
6. 6
   Extracciónthe aqueous phase extracted with toluene (40 ml)
7. 7
   OtroThe combined organic phases were evaporated
8. 8
   Otroto give a solid which
9. 9
   Otrowas recrystallised from toluene/petroleum ether (100°-120° C.) (1:1 v/v)

Procedimiento

A mixture of 4-methylphenyl boronic acid (9.7 g; 71 mmol), sodium carbonate (16.7 g; 158 mmol), water (100 ml), methanol (50 ml) and toluene (50 ml) was heated to 60° C. to give a clear solution. Compound C (20.0 g; 55 mmol) was then added, followed by tetrakis(triphenylphosphine)palladium (0.3 g; 0.25 mmol) and the mixture heated at reflux for 3 hours. Toluene (30 ml) was added and the warm mixture was filtered through diatomaceous earth. The organic phase was separated and the aqueous phase extracted with toluene (40 ml). The combined organic phases were evaporated to give a solid which was recrystallised from toluene/petroleum ether (100°-120° C.) (1:1 v/v) to give 5-(4'-methylbiphenyl-2-yl)-1-(4-nitrophenyl)-1H-tetrazole (D) (18.7 g; 90% yield), m.p. 164°-166° C.; NMR (CDCl3): 2.3(3H, s), 6.45(2H, d), 6.85(4H, m), 7.38(1H, d), 7.65(2H, m), 7.85(1H, d), 8.0(2H, d).

Fuente