Water → 1-Bromo-4-(1-bromoethyl)benzene

To a solution of 1-(4-bromophenyl)ethanol (1 g, 5 mmol) in tetrahydrofuran (80 mL) was added dropwise tribromophosphine (669 mg, 2.5 mmol) at 0° C. The solution was stirred at room temperature for 2 hours, and then water was added to quench the reaction at 0° C. The mixture was extracted with ethyl acetate (20 mL×3). The organic layers were combined and concentrated to give a residue. And the residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:50) to give 1-bromo-4-(1-bromoethyl)benzene as an oil (780 mg, 59%). 1H NMR (300 MHz, CD3OD): δ 7.46 (d, J=8.1 Hz, 2H), 7.36 (d, J=8.1 Hz, 2H), 5.25 (q, J=6.9 Hz, 1H), 1.98 (d, J=6.9 Hz, 3H).

1. customto quench
2. customthe reaction at 0° C
3. extractionThe mixture was extracted with ethyl acetate (20 mL×3)
4. concentrationconcentrated
5. customto give a residue
6. customAnd the residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:50)

ORD-Eintrag

ord-44ad3735b5ef4ce689cfbf28b07a9811

Quelldatensatz

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09206128B2