Aluminum(III) Chloride → 5'-Hydroxy-2'-iodo-4'-methoxyacetophenone

Participants

Reaction Conditions

Reaction Steps

A solution of ketone 9 (625 mg, 1.87 mmol) in dry CH2Cl2 (5 mL), was treated with AlCl3 (325 mg, 2.44 mmol) and the resulting mixture stirred at 18° C. under a nitrogen atmosphere for 21 h then partitioned between H2O (10 mL) and additional CH2Cl2 (10 mL). The separated aqueous phase was extracted with CH2Cl2 (1×10 mL) and the combined organic fractions were then dried (MgSO4), filtered and concentrated under reduced pressure. The ensuing residue was subjected to flash chromatography (1:4 v/v ethyl acetate/hexane elution) to afford the title compound 13 (411 mg, 75%) as a pale-yellow solid, m.p. 109.4-110.6° C., Rf 0.5 in 1:1 v/v ethyl acetate/hexane.

Provenance & Evidence