3-Ethylstyrene → 1-(2-Bromoethyl)-3-ethylbenzene

Temperatur

0 °C

To a solution of 3-ethyl-1-vinylbenzene (Preparation 20, 1.45 g, 10.9 mmol) in anhydrous tetrahydrofuran (50 ml) under nitrogen at 0° C. was added diborane (1.0M solution in tetrahydrofuran, 4 ml, 4 mmol) dropwise over 30 min. After 30 min at room temperature, methanol (0.1 ml) was added to destroy excess diborane. The reaction mixture was cooled to 0° C., and bromine (0.59 ml, 11 mmol) and a solution of sodium methoxide in methanol (12.1 mmol) were added via separate syringes at such a rate that a pale yellow coloration was always maintained. The reaction mixture was partitioned between aqueous saturated potassium carbonate solution and hexane. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined extracts were dried (MgSO4), filtered and concentrated in vacuo to afford the crude product. The residue was purified by silica column chromatography eluting with hexane to afford the title compound (640 mg, 28%).

1. customto destroy excess diborane
2. customvia separate syringes at such a rate that a pale yellow coloration
3. temperaturewas always maintained
4. customThe reaction mixture was partitioned between aqueous saturated potassium carbonate solution and hexane
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with dichloromethane
7. dry with materialThe combined extracts were dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto afford the crude product
11. customThe residue was purified by silica column chromatography
12. washeluting with hexane

ORD-Eintrag

ord-05edc4a1862240078977c9f8fc3a1a5f

Quelldatensatz

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06610711B2