反应详情

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.

1. temperaturecooled jacket
2. customThe stirring solution was degassed
3. customby bubbling nitrogen
4. customThe reaction was quenched with 10% Na2S2O3 and aqueous layer
5. extractionwas extracted with ethyl acetate
6. washCombined organic layers were washed with brine
7. dry with materialdried over Na2SO4 and volatiles
8. customwere removed under reduced pressure