Iodine → Phenanthrene

In a photoreaction container, argon was infused into a solution of 4.0 g (10.0 mmol) of stilbene in 7 L of acetonitrile at room temperature while stirring. After 10 minutes, 2.5 g (10.0 mmol, 1.0 eq.) of iodine and 28 mL (400.0 mmol, 40 eq.) of propylene oxide were added, followed by irradiation of light at room temperature while stirring. After 72 hours of irradiation, the disappearance of the raw materials was confirmed, and the resulting reaction liquid was concentrated. The residual product was dissolved in 500 mL of chloroform, followed by washing with 1 L of saturated sodium thiosulfate and 500 mL of brine. The organic layer was dried over magnesium sulfate, and then the solvent was distilled under reduced pressure to give a solid. The solid was collected by suction filtration using a Büchner funnel and a filtering flask, which was then washed with 50 mL of methanol twice. The solid was dried under reduced pressure at 60° C. to give 2.6 g (64%) of light brown powder.

1. customfollowed by irradiation of light at room temperature
2. stirringwhile stirring
3. customAfter 72 hours of irradiation
4. customthe resulting reaction liquid
5. concentrationwas concentrated
6. dissolutionThe residual product was dissolved in 500 mL of chloroform
7. washby washing with 1 L of saturated sodium thiosulfate and 500 mL of brine
8. dry with materialThe organic layer was dried over magnesium sulfate
9. distillationthe solvent was distilled under reduced pressure
10. customto give a solid
11. filtrationThe solid was collected by suction filtration
12. washwas then washed with 50 mL of methanol twice
13. customThe solid was dried under reduced pressure at 60° C.
14. customto give 2.6 g (64%) of light brown powder

ORD record

ord-9490af1ce2b14d7bb75ff164b66511b5

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174979B2