Phosphorus pentachloride → 3-({1-[1-(4-Chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)propane-1-sulfonyl chloride

Participants

Reaction Steps

3-({1-[1-(4-Chlorophenyl)cyclobutyl]-3,4-dihydroisoquinolin-7-yl}oxy)propane-1-sulfonic acid (8.4 g) were dissolved in dichloromethane (70 mL). Pentachloro-λ5-phosphane (6.05 g, 29 mmol) were added at room temperature and the reaction mixture was heated under reflux for 3 h. The reaction mixture was poured on ice water and the aqueous layer was extracted with dichloromethane. The combined organic layers were concentrated in vacuo (11 g). The crude product was used for the next step without further purification. For test purposes a sample of the crude product (3.8 g) was purified by flash chromatography (silica, methanol:acetonitrile=1:1) to yield a pale yellow foam (1.5 g).

Provenance & Evidence