Hydrochloric Acid → 9-Anthraceneboronic Acid

Temperature

-80 °C

In a 500 mL three-neck flask, 7.7 g (30 mmol) of 9-bromoanthracene was placed, and the air in the flask was replaced with nitrogen. Then, 200 mL of THF was added into the flask and the solution was cooled to −80° C. under nitrogen stream. After cooling, 18 mL (30 mmol) of 1.6 M n-butyllithium was dripped into the solution and stirred at the same temperature for 2 hours. After a certain period, 6.8 mL (60 mmol) of trimethyl borate was added into the solution, the temperature of the solution was raised to room temperature, and then, the solution was stirred for 17 hours. After a certain period, 100 mL of 1.0 M hydrochloric acid was added to the solution and stirred for 1 hour. An aqueous layer of the obtained mixture was extracted with ethyl acetate. The resulting extracted solution and the organic layer were combined and washed with saturated saline, and then the organic layer was dried with magnesium sulfate. The obtained mixture was gravity filtered, and the filtrate was condensed to give a solid. The solid was recrystallized with toluene, so that 5.2 g of target white powder was obtained in a yield of 80%.

1. temperatureAfter cooling
2. waitAfter a certain period
3. temperaturethe temperature of the solution was raised to room temperature
4. stirringthe solution was stirred for 17 hours
5. waitAfter a certain period
6. stirringstirred for 1 hour
7. extractionAn aqueous layer of the obtained mixture was extracted with ethyl acetate
8. extractionThe resulting extracted solution
9. washwashed with saturated saline
10. dry with materialthe organic layer was dried with magnesium sulfate
11. filtrationfiltered
12. customcondensed
13. customto give a solid
14. customThe solid was recrystallized with toluene, so that 5.2 g of target white powder
15. customwas obtained in a yield of 80%

ORD record

ord-b16b59506ac64110a00c617f3fd45e9e

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859108B2