Water → 5-(4'-Methyl[1,1'-biphenyl]-2-yl)-1-(4-nitrophenyl)-1H-tetrazole

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-methylphenyl boronic acid (9.7 g; 71 mM), sodium carbonate (16.7 g; 158 mM), 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 mM) was then added, followed by tetrakis(triphenylphosphine)palladium (0.3 g; 0.25 mM) and the mixture was heated under 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 was 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(2 H, d), 6.85(4H, m), 7.38(1H, d), 7.65(2H, m), 7.85(1H, d), 8.0(2H, d).

Provenance & Evidence