Hydrogen Peroxide → 4-(2-Bromophenyl)butan-1-ol

To a solution of 0.4 M 9-BBN in hexane (72 mL, 28.8 mmol) was added 4-bromophenyl-1-butene (3.99 g, 18.9 mmol) at room temperature. The resulting mixture was stirred at room temperature for 20 h. The mixture was treated sequentially with 3.3 mL of 6N aqueous NaOH (19.8 mmol), THF (7 mL), and 30% H2O2 in H2O (7 mL), then refluxed for 2 h. The reaction mixture was then cooled to room temperature. The organic layer was washed with aqueous sodium sulfite (40 mL), H2O (20 mL), and brine (20 mL). The aqueous extracts were combined, saturated with solid K2CO3 and extracted with Et2O (3×50 mL). The combined organic extracts were dried over Na2 SO4, filtered and concentrated. The resulting crude product was purified by flash chromatography twice (33% EtOAc in hexane and 20% EtOAc in hexane) to yield 4-(o-bromophenyl)butanol).

1. temperaturerefluxed for 2 h
2. temperatureThe reaction mixture was then cooled to room temperature
3. washThe organic layer was washed with aqueous sodium sulfite (40 mL), H2O (20 mL), and brine (20 mL)
4. extractionextracted with Et2O (3×50 mL)
5. customThe combined organic extracts were dried over Na2 SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe resulting crude product was purified by flash chromatography twice (33% EtOAc in hexane and 20% EtOAc in hexane)

ORD-Eintrag

ord-72f692e7e04f48b39f9995aa09c4becd

Quelldatensatz

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07053101B2