Acetic Acid → HCID 90310777, compound

Temperature

-78 °C

To a 100 mL round-bottomed flask were added a stir bar, dry THF (15.0 mL) and 2,2,6,6-tetramethylpiperidine (2.3 mL, 13.6 mmol). The flask was cooled to −78° C. (bath temp) and then treated with 2.5 M n-BuLi in hexanes (5.46 mL, 13.6 mmol) over 2 min. The resultant mixture was stirred for 5 min and then warmed to 0° Celsius. After 65 min, the mixture was re-cooled to −78° Celsius and treated with B(O-iPr)3 (17.5 mL, 13.6 mmol) over 4 min. After 20 min, a solution consisting of tert-butyl(2-(tert-butyl)-6-fluorophenoxy)dimethylsilane (2.57 g, 9.1 mmol) and dry THF (5.0 mL) was added over the course of 2 min and stirring continued for 3 hours. The reaction was gradually warmed to room temperature while stirring for 18 hours, after which time, HOAc (5.2 mL, 91 mmol) was added. The mixture was then poured into water and stirred for 5 min. The aqueous mixture was then extracted with EtOAc (200 mL), the extract dried over Na2SO4, filtered and concentrated to dryness. Purification by FCC yielded (4-(tert-butyl)-3-((tert-butyldimethylsilyl)oxy)-2-fluorophenyl)boronic acid (2.13 g, 72%).

1. additionTo a 100 mL round-bottomed flask were added a stir bar
2. temperaturewarmed to 0° Celsius
3. temperaturethe mixture was re-cooled to −78° Celsius
4. waitAfter 20 min
5. additionwas added over the course of 2 min
6. waitcontinued for 3 hours
7. temperatureThe reaction was gradually warmed to room temperature
8. stirringwhile stirring for 18 hours
9. stirringstirred for 5 min
10. extractionThe aqueous mixture was then extracted with EtOAc (200 mL)
11. dry with materialthe extract dried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated to dryness
14. customPurification by FCC

ORD record

ord-962b792248b84f2386d86ec27c7d120f

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073876B2