Benzene, 1-bromo-3-ethyl- → 3-Ethylstyrene

Temperature

75 °C

To a solution of 1-bromo-3-ethylbenzene (2.0 g, 10.8 mmol) in deoxygenated N,N-dimethylformamide (50 ml) under nitrogen was added tributylvinyltin (5.0 g, 16.2 mmol) and tetrakistriphenylphosphine palladium (0) (500 mg, 4 mol %) and the reaction mixture was heated to 75° C. for 7 h. The cooled reaction mixture was poured onto water (400 ml) and extracted with diethyl ether (5×200 ml). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo to afford the crude product. This was distilled under reduced pressure to afford a residue that was partitioned between water and hexane. The layers were separated and the aqueous layer was extracted with hexane. The combined extracts were dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a colourless oil (1.4 g, 98%).

1. customThe cooled reaction mixture
2. additionwas poured onto water (400 ml)
3. extractionextracted with diethyl ether (5×200 ml)
4. dry with materialThe combined extracts were dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto afford the crude product
8. distillationThis was distilled under reduced pressure
9. customto afford a residue that
10. customwas partitioned between water and hexane
11. customThe layers were separated
12. extractionthe aqueous layer was extracted with hexane
13. dry with materialThe combined extracts were dried (MgSO4)
14. filtrationfiltered
15. concentrationconcentrated in vacuo

ORD record

ord-ce80f71b5d28447cbc00cf4d9786e3a5

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610711B2