反応 #81055

反応方程式

4-Bromo-5-methoxy-3-[3-(trifluoromethyl)phenyl]pyridazine

vinyltributyltin

→

4-ethenyl-5-methoxy-3-[3-(trifluoromethyl)phenyl]pyridazine

収率 42.0%

溶媒

DMF

反応条件

後処理

1. 1
   温度The reaction was then cooled
2. 2
   その他partitioned between aqueous KF and ethyl acetate
3. 3
   抽出The KF solution was extracted with additional ethyl acetate
4. 4
   洗浄The organic layers were washed with brine
5. 5
   乾燥dried (MgSO4)
6. 6
   ろ過filtered through silica gel
7. 7
   その他evaporated in vacuo
8. 8
   その他The crude oil was then chromatographed on a Prep-500

実験手順

4-Bromo-5-methoxy-3-[3-(trifluoromethyl)phenyl]pyridazine (1.0 g, 0.003 mole, Compound No. 57), vinyltributyltin (1.1 g, 0.0034 mole) and trans-benzyl(chloro)bis-(triphenylphosphine)-palladium(II) (20 mg) were heated to 110° C. in DMF (50 mL) under N2 for 4 h. The reaction was then cooled and partitioned between aqueous KF and ethyl acetate. The KF solution was extracted with additional ethyl acetate. The organic layers were washed with brine, dried (MgSO4), filtered through silica gel and then evaporated in vacuo. The crude oil was then chromatographed on a Prep-500 to give 4-ethenyl-5-methoxy-3-[3-(trifluoromethyl)phenyl]pyridazine (0.35 g, 42% yield, Compound No. 55) as a light brown solid.

出典