Phosphorus tribromide → 5-Bromo-2-(bromomethyl)-1,3-difluorobenzene
Reaktionsgleichung
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH2:9]O)=[C:4]([F:11])[CH:3]=1.[Br:12]P(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH2:9][Br:12])=[C:4]([F:11])[CH:3]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of (4-bromo-2,6-difluorophenyl)methanol (2 g, 8.97 mmol) in DCM (80 mL) was added tribromophosphine (2.91 g, 10.76 mmol) at 0° C. The resulting mixture was stirred at rt. After LCMS analysis showed the starting material had disappeared, the mixture was washed with aq NaHCO3 (40 mL) and brine (30 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The crude material was purified by silica column chromatography (PE/EA=5/1) to yield a colorless oil of 5-bromo-2-(bromomethyl)-1,3-difluorobenzene (1.6 g, 5.48 mmol, 61.2% yield): 1H NMR (400 MHz, CD3OD) δ 7.12 (d, J=6.8 Hz, 2H), 4.47 (s, 2H).