Bromide ion → HCID 67280155, compound

A 100 ml portion of a solution of the product from example 10 step (i) (120.7 g) in THF (500 ml) was added to a stirred mixture of magnesium turnings (13.4 g) in THF (100 ml). Dibromoethane (0.2 ml) was added, and the mixture gently refluxed on initiation. The remaining bromide solution was added dropwise maintaining the reaction at reflux. After addition the mixture was allowed to cool to RT then transferred via cannula into a stirred solution of trimethylborate (112 ml) in TIE (200 ml) at 0° C. The mixture was warmed to RT, stirred for 2 h then quenched with 2M hydrochloric acid (300 ml). After stirring at RT for 18 h the THF was removed under reduced pressure and the mixture extracted with diethylether. The organics were separated, washed with water, dried and evaporated under reduced pressure. The residue was triturated with diethylether/isohexane and filtered. Yield 53.02 g

1. temperaturethe mixture gently refluxed on initiation
2. temperaturemaintaining
3. customthe reaction
4. temperatureat reflux
5. additionAfter addition the mixture
6. temperatureThe mixture was warmed to RT
7. customthen quenched with 2M hydrochloric acid (300 ml)
8. stirringAfter stirring at RT for 18 h the THF
9. customwas removed under reduced pressure
10. extractionthe mixture extracted with diethylether
11. customThe organics were separated
12. washwashed with water
13. customdried
14. customevaporated under reduced pressure
15. customThe residue was triturated with diethylether/isohexane
16. filtrationfiltered

ORD record

ord-bbe4a1ad82d2442a8fdb31379917bd00

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158820B2