Phosphorus tribromide → 2-(Bromomethyl)-1-methyl-4-nitrobenzene

To a slight suspension of (2-methyl-5-nitrophenyl)methanol (2.0 g, 12 mmol) in DCM (20 ml) in an ice-water bath under nitrogen was a added a solution of phosphorus tribromide (1.13 mL, 12 mmol, Aldrich) in DCM (20 ml). The resulting solution was allowed to warm to ambient temperature and stirred for 45 min. The solution was poured onto a mixture of ice-water (50 ml) and saturated sodium hydrogen carbonate (50 ml). The biphasic mixture was diluted with dichloromethane (50 ml) and the phases separated. The aqueous phase was extracted with dichloromethane (20 ml). The combined organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo to give 2-(bromomethyl)-1-methyl-4-nitrobenzene as a pale yellow solid (1.81 g).

1. customthe phases separated
2. extractionThe aqueous phase was extracted with dichloromethane (20 ml)
3. dry with materialThe combined organic extracts were dried (MgSO4)
4. filtrationfiltered
5. customthe solvent removed in vacuo

ORD-Eintrag

ord-238a4e5248be4c31b67678f9d92a5e07

Quelldatensatz

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08399436B2