Hydrogen Bromide → HCID 71086867, compound

To a 50 mL round bottom flask adapted for magnetic stirring and fitted with a reflux condenser is charged 5-(3-fluorophenyl)-3-methoxy-2-cyanopyridine, 9, (0.912 g, 4 mmol) and a 48% aqueous solution of HBr (10 mL). While being stirred, the reaction solution is heated to reflux for 20 hours. The reaction can be determined to be complete due to the disappearance of 5-(3-fluorophenyl)-3-methoxy-2-cyanopyridine as measured by TLC analysis using hexane/ethyl acetate (6:3) as the mobile phase and UV 435 nm to visualize the reaction components. The reaction is then cooled to 0° C. to 5° C. with stirring and the pH is adjusted to approximately 2 by the slow addition of 50% aqueous NaOH. Stirring is then continued at 0° C. to 5° C. for 3 hours. The resulting solid is collected by filtration and washed with water, then hexane. The resulting cake is dried in vacuo at 40° C. to afford the desired product.

1. customTo a 50 mL round bottom flask adapted
2. customfitted with a reflux condenser
3. stirringWhile being stirred
4. temperaturethe reaction solution is heated
5. temperatureto reflux for 20 hours
6. customThe reaction
7. customthe reaction components
8. temperatureThe reaction is then cooled to 0° C. to 5° C.
9. stirringwith stirring
10. stirringStirring
11. filtrationThe resulting solid is collected by filtration
12. washwashed with water
13. customThe resulting cake is dried in vacuo at 40° C.

ORD record

ord-21e41535fba549c3812c2855f9d7d659

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865748B2