Triphenylphosphine → Benzene, ((2-bromoethoxy)methyl)-

Participants

Reaction Steps

To a stirred solution of 2-(benzyloxy)ethanol (17.0 g, 111.84 mmol) and PPh3 (35.0 g, 134.21 mmol) in DCM (170 mL) at −10° C. to −5° C., NBS (23.88 g, 134.21 mmol) was added slowly in portions maintaining the temperature at −10° C. to −5° C. After addition, the reaction mixture was allowed to stir at RT for 1 h until complete consumption starting material, as evidenced by TLC analysis. The reaction mixture was concentrated, the obtained crude compound was purified by CC using 5% EtOAc in PE as eluent to afford ((2-bromoethoxy)methyl)benzene (13.5 g, 56.2%) as pale yellow liquid (TLC solvent system: 30% EtOAc in PE; Rf: 0.7).

Provenance & Evidence