Hydrochloric Acid → (6-Phenyldibenzo[b,d]thiophen-4-yl)boronic acid

Temperature

-78 °C

3.5 g (13.4 mmol) 4-phenyldibenzothiophene was dissolved in ˜30 mL anhydrous THF in a three necked 250 mL flask and cooled down to −78° C. To the mixture, 17 mL (27 mmol) 1.6 M BuLi in hexane was added and stirred for 30 minutes. The cooling batch was removed and let reaction kept stirring for overnight. The reaction mixture was cooled down again to −78° C. and 4.5 mL (40 mmol) trimethyl borate was added and stirred at room temperature for 4 hours. ˜100 1M HCl was added and kept stirring for 1 hour. The mixture was extracted by ethyl acetate and the organic extracts were combined. The solvent was evaporated to dryness. The solid was added with ˜100 mL 20% ethyl acetate in hexane was stirred for few hours and then filtered. The filtered solid washed by hexane few times. ˜2.5 g white solid was obtained as product which was confirmed by proton NMR.

1. customThe cooling batch was removed
2. customreaction
3. stirringkept stirring for overnight
4. temperatureThe reaction mixture was cooled down again to −78° C.
5. stirringstirred at room temperature for 4 hours
6. stirringkept stirring for 1 hour
7. extractionThe mixture was extracted by ethyl acetate
8. customThe solvent was evaporated to dryness
9. additionThe solid was added with ˜100 mL 20% ethyl acetate in hexane
10. stirringwas stirred for few hours
11. filtrationfiltered
12. washThe filtered solid washed by hexane few times

ORD record

ord-ac43432432fb4bbca3fc5a1593fac2f2

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822708B2