Hydrochloric Acid → HCID 71743724, compound

Temperature

-78 °C

To a stirred solution of 2-bromo-5-fluoro-benzonitrile (1 g, 5 mmol) and Ti(Oi-Pr)4 (1.81 mL, 5.5 mmol) in ether (20 mL) was added EtMgBr (3.67 mL, 11 mmol) at −78° C. After stirring at −78° C. for 10 min, the solution was warmed up to room temperature and stirred for 1 hour. BF3-Et2O (1.25 mL) was added before it was stirred for another 1 hour. After addition of 1 N aq. HCl (15 mL) and ether (30 mL), aq. NaOH (10%, 45 mL) solution was added to give two clear phases. The mixture was exacted with EtOAc (30 mL×5). The combined organic layers were dried over anhy. Na2SO4, filtered, and concentrated in vacuo to give a crude product, which was purified by column chromatography (PE:EA=5:1) to afford the title compound (800 mg, 70%) as oil.

1. temperaturethe solution was warmed up to room temperature
2. stirringstirred for 1 hour
3. stirringwas stirred for another 1 hour
4. additionwas added
5. customto give two clear phases
6. customThe combined organic layers were dried over anhy
7. filtrationNa2SO4, filtered
8. concentrationconcentrated in vacuo
9. customto give a crude product, which
10. customwas purified by column chromatography (PE:EA=5:1)

ORD record

ord-49c6bb4a61864939aefb4c8e0a455a29

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133158B2