Phosphorus tribromide → 1-Bromo-6-(bromomethyl)naphthalene

Temperatur

0 °C

To a stirred suspension of 5-bromo-2-hydroxymethylnaphthalene (7.00 g, 29.5 mmol) in dry Et2O (100 mL) at 0° C. was added PBr3 (8.91 g, 33 mmol) in portions over 20 minutes. The reaction was stirred for an additional 30 minutes at 0° C., diluted with Et2O (100 mL) and quenched with H2O (100 mL) over 20 minutes. The heterogeneous solution was diluted further with H2O (100 mL) and the layers separated. The aqueous phase was extracted with Et2O (1×200 mL) and the combined organic layers were washed with H2O (1×100 mL) and saturated NaCl (1×100 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by preparative HPLC (SiO2 : gradient hexane/EtOAc) to give the title compound as a white solid (4.60 g, 52%).

1. customquenched with H2O (100 mL) over 20 minutes
2. additionThe heterogeneous solution was diluted further with H2O (100 mL)
3. customthe layers separated
4. extractionThe aqueous phase was extracted with Et2O (1×200 mL)
5. washthe combined organic layers were washed with H2O (1×100 mL) and saturated NaCl (1×100 mL)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo
8. customThe residue was purified by preparative HPLC (SiO2 : gradient hexane/EtOAc)

ORD-Eintrag

ord-ea1270c7ed6a4214b115ff415b1b01c4

Quelldatensatz

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04895861