Phosphorus pentachloride → HCID 13505373, compound

Participants

Reaction Steps

A solution of 1.47 g of PCl5 (7.08 mmol, 1 eq.) in 35 mL of 1,2-dichloroethane was cooled to 0° under N2, then 2.00 g of 2-iodo-4-chlorobenzoic acid (7.08 mmol), 1 eq.) was added neat, at once. The bath was removed, the reaction allowed to warm to 25° and maintained there for 3 hr. The volatiles were removed in vacuo, the residue dissolved in 35 mL of fresh 1,2-chloroethane and again evaporated. The residual oil was dissolved in 70 mL of benzene, cooled to 0° and treated with 0.94g of AlCl3 (7.08 mmol, 1 eq.). After 1 hr at 0°, the reaction was allowed to warm to 25° and maintained there overnight. The mixture was poured onto 200 mL of ice, warmed and extracted with Et2O (3×100 mL). The combined Et2O layers were washed with saturated NaHCO3 (2×200 mL), saturated NaCl (1×300 mL), dried (MgSO4), and the solvents removed in vacuo to yield 2.00 g (82%) of 4-chloro-2-iodobenzophenone as a yellow oil.

Provenance & Evidence