Reaction #574594

Reaction equation

4-methylphenyl boronic acid

sodium carbonate

water

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

Compound C

→

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

Yield 95.1%

Solvents

toluene

methanol

Toluene

Conditions

Workup

1. 1
   Otherto give a clear solution
2. 2
   Temperaturethe mixture heated
3. 3
   Temperatureat reflux for 3 hours
4. 4
   Filtrationthe warm mixture was filtered through diatomaceous earth
5. 5
   OtherThe organic phase was separated
6. 6
   Extractionthe aqueous phase extracted with toluene (40 ml)
7. 7
   OtherThe combined organic phases were evaporated
8. 8
   Otherto give a solid which
9. 9
   Otherwas recrystallised from toluene/petroleum ether (100°-120° C.) (1:1 v/v)

Procedure

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).

Source