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 1 M 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 stinrred for few hours and then filtered. The filtered solid washed by hexane few times. ˜2.5

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. waitwas stinrred for few hours
11. filtrationfiltered
12. washThe filtered solid washed by hexane few times

ORD record

ord-356323c848f44822be613f8331eef53a

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367850B2