تفاعل #50323

معادلة التفاعل

bromomethyl biphenyl

2-butylimidazole

2-butyl imidazole

potassium tert-butoxide

→

biphenyl imidazole

المردود 98.8%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 16 h
2. 2
   تركيزconcentrated in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in chloroform
4. 4
   غسيلwashed with water
5. 5
   استخلاصThe aqueous layer was extracted with fresh chloroform
6. 6
   تجفيفthe combined extracts were dried (MgSO4)
7. 7
   تركيزconcentrated in vacuo
8. 8
   أخرىThe residue was purified by chromatography

الإجراء التجريبي

To a solution of 4.07 g (32.8 mmol) of 2-butylimidazole (obtained from step 1) in 110 mL of DMF was added 44.3 mL (44.3 mmol) of potassium tert-butoxide (1M in THF), and the resulting solution was stirred at room temperature for 15 min. To the dark brown mixture was added 20.1 g (36.1 mmol) of the bromomethyl biphenyl. The reaction mixture was stirred at room temperature for 16 h, and concentrated in vacuo. The residue was dissolved in chloroform and washed with water. The aqueous layer was extracted with fresh chloroform, and the combined extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography to give 7.2 g (37%) of the biphenyl imidazole intermediate as a yellow oil which solidified as a glass: 1H NMR (CDCl3) δ 0.90 (t, J=7.31 Hz, 3H), 1.35 (septet, J=7.5 Hz, 2H), 1.71 (quintet, J=7.74 Hz, 2H), 2.61 (t, J=7.58 Hz, 2H), 4.93 (s, 2H), 6.65 (d, J=1.35 Hz, 1H), 6.79 (d, J=8.31 Hz, 2H), 6.92 (d, J=7.3 Hz, 6H), 6.97 (d, J=1.32 Hz, 1H), 7.11 (d, J=8.2 Hz, 2H), 7.2-7.4 (m, 10H), 7.4-7.55 (m, 2H), 7.95 (dd, J=6.85, 2.08 Hz, 1H); MS(FAB) m/e (relative intensity) 607 (100, M+Li), 601 (90, M+H).

المصدر