2-Bromobenzyl bromide → 2-(But-3-en-1-yl)bromobenzene

To an ice cold solution of 2-bromobenzyl bromide (5.00 g, 0.020 mol) in THF (25 mL) was added 1M allyl magnesium bromide (100 mL, 0.100 mol) slowly via cannula. The reaction mixture was stirred at reflux for 1.5 h, cooled in an ice bath and quenched with 50 mL of aqueous 2M H2SO4. Water (50 mL) was added to dissolve any remaining solid and the layers were separated. The aqueous layer was extracted with Et2O (2×150 mL). The combined organic extracts Were dried over Na2SO4, filtered and concentrated to yield 1-bromo-2-but-3-enyl-benzene as a light yellow oil. The isolated crude product was carried forward without further purification.

1. temperatureat reflux for 1.5 h
2. temperaturecooled in an ice bath
3. customquenched with 50 mL of aqueous 2M H2SO4
4. additionWater (50 mL) was added
5. dissolutionto dissolve any remaining solid
6. customthe layers were separated
7. extractionThe aqueous layer was extracted with Et2O (2×150 mL)
8. dry with materialThe combined organic extracts Were dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-ed0ffa8b47004e11a7fec2e6b4636536

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07053101B2