Phosphorus tribromide → 4-Bromo-1-(bromomethyl)-2-ethylbenzene

To a solution of (4-bromo-2-ethyl-phenyl)-methanol (7.9 g, 36.7 mmol) in anhydrous CHCl3 (122 mL) was added PBr3(4.2 mL, 44.1 mmol). The resulting mixture was stirred at room temperature for 2 hours before it was quenched by the addition of water. The organic layer was washed with NaHCO3, brine and dried over MgSO4. The solvent was removed in vacuo and the residue was filtered through a pad of silica gel with 20% EtOAc in hexanes. The solvent was removed in vacuo to afford the desired product (8.4 g, 83%). 1H NMR (300 MHz, CDCl3): δ 1.29 (t, J=7.5 Hz, 3 H), 2.71–2.78 (m, 2 H), 4.48 (s, 2H), 7.17–7.20 (m, 1H), 7.29–7.32 (m, 1 H), 7.36–7.38 (m, 1H).

1. customwas quenched by the addition of water
2. washThe organic layer was washed with NaHCO3, brine
3. dry with materialdried over MgSO4
4. customThe solvent was removed in vacuo
5. filtrationthe residue was filtered through a pad of silica gel with 20% EtOAc in hexanes
6. customThe solvent was removed in vacuo

ORD record

ord-629c561ac52f44919310e17607ab23be

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07151105B2