Aluminum(III) Chloride → 1-(2-Bromo-5-hydroxy-4-methoxyphenyl)ethan-1-one

Participants

Reaction Conditions

Reaction Steps

A solution of ketone 38 (220 mg, 0.766 mmol) in dry CH2Cl2 (2.0 mL) was treated with AlCl3 (306 mg, 2.29 mmol) and the resulting mixture stirred at 18° C. under a nitrogen atmosphere for 2 h. The ensuing mixture was partitioned between H2O (5 mL) and CH2Cl2 (5 mL) then the separated aqueous phase extracted with CH2Cl2 (1×15 mL). The combined organic fractions were dried (MgSO4), filtered and concentrated under reduced pressure and the ensuing residue subjected to flash chromatography (15:85 v/v ethyl acetate/hexane elution) to afford the title compound 39 (184 mg, 98%) as a pale-yellow solid, m.p. 109.7-111.4° C., Rf 0.4 in 1:1 v/v ethyl acetate/hexane.

Provenance & Evidence