反応 #636660

反応方程式

water

1-bromo-4-[2-(4-chlorophenyl)vinyl]benzene

propylene oxide

iodine

→

3-bromo-6-chlorophenanthrene

収率 100.9%

溶媒

THF

cyclohexane

反応条件

後処理

1. 1
   温度cooled jacket
2. 2
   その他The stirring solution was degassed
3. 3
   その他by bubbling nitrogen
4. 4
   その他The reaction was quenched with 10% Na2S2O3 and aqueous layer
5. 5
   抽出was extracted with ethyl acetate
6. 6
   洗浄Combined organic layers were washed with brine
7. 7
   乾燥dried over Na2SO4 and volatiles
8. 8
   その他were removed under reduced pressure

実験手順

A 2 L vessel equipped with a pyrex inner water-cooled jacket was charged with 5.16 g (17 mmol) of 1-bromo-4-[2-(4-chlorophenyl)vinyl]benzene from Step 1, 2 L of cyclohexane, 25 mL of THF, 25 mL of propylene oxide and 6.7 g (26 mmol) of iodine. The stirring solution was degassed by bubbling nitrogen and was exposed to UV light for 24 hrs by inserting a 450 W medium pressure mercury lamp in the inner. The reaction was quenched with 10% Na2S2O3 and aqueous layer was extracted with ethyl acetate. Combined organic layers were washed with brine, dried over Na2SO4 and volatiles were removed under reduced pressure. The residue was swished in a minimal amount of ethyl acetate to afford approx. 5 g of 3-bromo-6-chlorophenanthrene as a solid.

出典