Hydrochloric Acid → Benzo[c]phenanthren-5-ylboronic acid

Temperature

-40 °C

A flask was charged with 10.1 g of 5-bromobenzo[c]phenanthrene in an argon atmosphere. 400 mL of dehydrated diethyl ether was then added to the flask. After cooling the reaction solution to −40° C., 22 mL of a 1.6 M hexane solution of n-butyllithium was added to the reaction solution. The mixture was heated to 0° C., and stirred for 1 hour. After cooling the reaction solution to −60° C., a dehydrated diethyl ether (10 mL) solution of 14.4 g of triisopropyl borate was added dropwise to the reaction solution. The reaction solution was stirred for 5 hours while warming the reaction solution up to room temperature. After the addition of 100 mL of a 10% hydrochloric acid aqueous solution, the mixture was stirred for 1 hour. After removing the aqueous phase, the organic phase was washed with water and a saturated sodium chloride solution, and dried over magnesium sulfate. After removing magnesium sulfate by filtration, the organic phase was concentrated. The resulting solid was washed with hexane to obtain 5.37 g of the target benzo[c]phenanthrene-5-boronic acid (yield: 60%).

1. temperatureThe mixture was heated to 0° C.
2. temperatureAfter cooling the reaction solution to −60° C.
3. stirringThe reaction solution was stirred for 5 hours
4. temperaturewhile warming the reaction solution up to room temperature
5. stirringthe mixture was stirred for 1 hour
6. customAfter removing the aqueous phase
7. washthe organic phase was washed with water
8. dry with materiala saturated sodium chloride solution, and dried over magnesium sulfate
9. customAfter removing magnesium sulfate
10. filtrationby filtration
11. concentrationthe organic phase was concentrated
12. washThe resulting solid was washed with hexane

ORD record

ord-25b4d3575b4940a48aed5ad581feb6c4

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08803420B2