Hydrochloric Acid → 6-(Dibenzofuran-2-yl)naphthalene-2-ylboronic acid

Temperatur

-60 °C

In argon atmosphere, a liquid mixture of 7.47 g (20.0 mmol) of 2-(6-bromonaphthalene-2-yl)dibenzofuran and 75 ml of dry THF was cooled to −60° C., and 15.5 ml (24.0 mmol) of a 1.55 M hexane solution of n-butyllithium was added dropwise under stirring. Further, the reaction mixture was stirred at −70° C. for 2 h. The reaction solution was cooled again to −70° C., and 11.29 g (60.0 mol) of triisopropyl borate was added dropwise. The reaction mixture was heated up to room temperature, stirred for one hour, and left standing overnight. The reaction mixture was cooled on an ice bath, added with a 6 N hydrochloric acid, and stirred at room temperature for one hour. After adding dichloromethane, the reaction mixture was allowed to separate into liquid phases, and the organic phase was washed with water and dried over sodium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was purified by silica gel chromatography to obtain 4.20 g (yield: 62%) of 6-(dibenzofuran-2-yl)naphthalene-2-ylboronic acid.

1. stirringFurther, the reaction mixture was stirred at −70° C. for 2 h
2. temperatureThe reaction solution was cooled again to −70° C.
3. temperatureThe reaction mixture was heated up to room temperature
4. stirringstirred for one hour
5. waitleft
6. temperatureThe reaction mixture was cooled on an ice bath
7. stirringstirred at room temperature for one hour
8. customto separate into liquid phases
9. washthe organic phase was washed with water
10. dry with materialdried over sodium sulfate
11. customThe solvent was removed by distillation under reduced pressure
12. customthe residue was purified by silica gel chromatography

ORD-Eintrag

ord-5fe79d467b1a410faa3be13d5766254c

Quelldatensatz

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08940412B2