反応 #349264

反応方程式

2-bromo-3-phenyl-4-benzofuranacetic acid

cyclohexene

dinitrogen tetroxide

→

2-nitro-3-phenyl-4-benzofuranacetic acid

溶媒

chloroform

chloroform

反応条件

後処理

1. 1
   workup.WAITat 50°-55° C. for about 20 minutes
2. 2
   洗浄The mixture is washed with water
3. 3
   workup.ADDITIONthe organic layer is treated with an aqueous base
4. 4
   抽出extracted with dichloromethane
5. 5
   洗浄The organic layer is washed thrice with water
6. 6
   その他dried
7. 7
   その他evaporated
8. 8
   その他Two recrystallizations from benzene

実験手順

A solution of 2-bromo-3-phenyl-4-benzofuranacetic acid (12.1 g., 0.0365 mole) and cyclohexene (3.3 g., 0.04 mole) in 100 ml. of chloroform is treated with 5 g. of dinitrogen tetroxide in 20 ml. of chloroform dropwise. The mixture is stirred for 16 hours at about 25° C. then at 50°-55° C. for about 20 minutes. The mixture is washed with water, and the organic layer is treated with an aqueous base. The aqueous layer is acidified, then extracted with dichloromethane. The organic layer is washed thrice with water, dried and evaporated. Two recrystallizations from benzene give light yellow solid 2-nitro-3-phenyl-4-benzofuranacetic acid, m.p. 187.5°-189.5° C.

出典