Carbon tetrabromide → 2-Nitrophenethyl bromide

Participants

Reaction Steps

To a solution of 1-(2-hydroxyethyl)-2-nitrobenzene (21 ml, 150 mmol) and triphenylphosphine (39.2 g, 150 mmol) in DCM (400 ml) at 0° C. was add CBr4 (49.5 g, 150 mmol) in portions and the reaction mixture was stirred from 0° C. to RT overnight. The reaction mixture was quenched with sat. aq. Na2CO3, the layers were separated and the organic layer was washed with brine, dried (MgSO4) and evaporated to dryness. The residue was treated with EtOAc and the precipitated Ph3O was filtered and the solvent removed. This was repeated twice more. Purification by column chromatography (0% to 10% EtOAc in Hx) gave an oil that solidified on standing.

Provenance & Evidence