4-Chlorophenol → 4-(4-Chlorophenoxymethyl)-benzylazide

Participants

Reaction Conditions

Reaction Steps

Triphenylphosphine (4.33 g, 16.5 mmol) was dissolved in dry THF (20 mL) under an atmosphere of argon. After cooling to −40° C., diisopropyl-azodicarboxylate (DIAD, 3.2 mL, 16.5 mmol) was added and the mixture was stirred at −40° C. for 10 min. A solution of 4-chlorophenol (2.12 g, 16.5 mmol) and (4-azidomethyl-phenyl)-methanol (2.45 g, 15 mmol) in dry THF (10 mL) was added dropwise. After addition, the cooling bath was removed and stirring was continued for 1 h. The solution was diluted with Et2O (150 mL) and washed with pH-7-phosphate buffer solution (1×50 mL). The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The resulting residue was purified by flash chromatography (2-3% EtOAc in hexane) to give the title compound.

Provenance & Evidence