Allyl bromide → HCID 66762615, compound

Temperature

0 °C

At 0° C., isobutylmagnesium bromide (2.0 M ether solution, 1.2 eq.) and n-butyl lithium (2.5 M hexane solution, 2.4 eq.) were added to anhydrous THF (0.3 M). After stirring at 0° C. for 30 min, the reaction mixture was cooled to −40° C. and tert-butyl 5-bromo-2-chlorobenzoate from the previous step (1 eq.) was added over 15 min. The now red solution was stirred at −40° C. for 1 h before copper (I) cyanide (30% loading) was added. The resulting suspension was stirred at −40° C. for 15 min and then added allyl bromide (3 eq.). After stirring at −40° C. for another 2 h, the reaction mixture was quenched with sat. aq. NH4Cl and warmed to RT. The biphasic mixture was poured into more sat. aq. NH4Cl and extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a brown oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→19:1 (v/v) Hex:ether) afforded the title compound as a light yellow oil.

1. temperaturethe reaction mixture was cooled to −40° C.
2. additionwas added
3. stirringThe resulting suspension was stirred at −40° C. for 15 min
4. stirringAfter stirring at −40° C. for another 2 h
5. customthe reaction mixture was quenched with sat. aq. NH4Cl
6. temperaturewarmed to RT
7. additionThe biphasic mixture was poured into more sat. aq. NH4Cl
8. extractionextracted with ether
9. washThe combined organic extracts were washed with brine
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. customConcentration of the filtrate in vacuo afforded a brown oil
13. customPurification of the crude product
14. customthus obtained by way of flash chromatography (SiO2, Hex→19:1 (v/v) Hex:ether)

ORD record

ord-19e6d5df9ee24a7b84dde7ff858a961c

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063105B2