Allyl bromide → HCID 13685577, compound

Temperature

0 °C

A 500-mL four neck round-bottom flask was purged and maintained with an inert atmosphere of nitrogen, then a suspension of sodium hydride (14.0 g, 350 mmol, 2.01 equiv, 60%) in N,N-dimethylformamide (100 mL) was added. The mixture was cooled to 0° C., then a solution of pent-4-en-2-ol (15.0 g, 174 mmol, 1.00 equiv) in N,N-dimethylformamide (100 mL) was added drop-wise and the mixture was stirred for 20 min at 0° C. The mixture was cooled to −20° C. and a solution of 3-bromoprop-1-ene (20.9 g, 172 mmol, 0.99 equiv) in N,N-dimethylformamide (100 mL) was added. The resulting mixture was allowed to warm to room temperature and stirred overnight, then carefully quenched with H2O (500 mL). The aqueous was extracted with ethyl acetate (4×100 mL) and the combined organics was washed with brine (2×200 mL), dried (Na2SO4), filtered and concentrated in vacuo to obtain the title compound as a yellow oil (13.3 g, 61%).

1. customA 500-mL four neck round-bottom flask was purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. additionwas added
4. temperatureThe mixture was cooled to −20° C.
5. temperatureto warm to room temperature
6. stirringstirred overnight
7. customcarefully quenched with H2O (500 mL)
8. extractionThe aqueous was extracted with ethyl acetate (4×100 mL)
9. washthe combined organics was washed with brine (2×200 mL)
10. dry with materialdried (Na2SO4)
11. filtrationfiltered
12. concentrationconcentrated in vacuo

ORD record

ord-2f1ec666291b4dcf896b75e9f8f37419

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871790B2