4-Chlorophenol → 2-[3-(4-Chloro-phenoxymethyl)-benzyl]-phthalimide

Participants

Reaction Conditions

Reaction Steps

Triphenylphosphine (280 mg, 1.07 mmol) was dissolved in dry THF (2 mL) under an atmosphere of argon. After cooling to −40° C., DIAD (0.21 mL, 1.07 mmol) was added and the mixture was stirred at −40° C. for 10 min. A solution of 4-chlorophenol (138 mg g, 1.07 mmol) and 2-(3-hydroxymethylbenzyl)-phthalimide (261 mg, 0.98 mmol) in dry THF (3 mL) was added dropwise. After addition, the cooling bath was removed and stirring was continued for 2 h. The solution was diluted with Et2O (40 mL) and washed with pH-7-phosphate buffer solution (1×20 mL). The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The resulting residue was purified by flash chromatography (EtOAc/hexane 1:5) to give the title compound.

Provenance & Evidence