反応 #65893

反応方程式

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

収率 95.1%

溶媒

toluene

methanol

Toluene

反応条件

後処理

1. 1
   その他to give a clear solution
2. 2
   温度the mixture heated
3. 3
   温度at reflux for 3 hours
4. 4
   ろ過the warm mixture was filtered through diatomaceous earth
5. 5
   その他The organic phase was separated
6. 6
   抽出the aqueous phase extracted with toluene (40 ml)
7. 7
   その他The combined organic phases were evaporated
8. 8
   その他to give a solid which
9. 9
   その他was recrystallised from toluene/petroleum ether (100°-120° C.) (1:1 v/v)

実験手順

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).

出典