4-Bromoanisole → 6-[4-methoxyphenyl]-2-(1H)-quinolone

Participants

Reaction Steps

A solution of t-butyl lithium (9.0 cm3 of a 2.0M solution in n-pentane) was added at -70° to a stirred solution of 4-bromoanisole (1.13 cm3) in tetrahydrofuran (THF) (20 cm3) under nitrogen. After 10 minutes a solution of anhydrous zinc chloride (1.23 g) in THF (10 cm3) was added and the mixture was allowed to warm to room temperature over 0.5 hour. A mixture of 6-iodo-2-(1H)-quinolone (0.813 g) and tetrakis(triphenylphosphine) palladium (0) (0.03 g) was added and the mixture was heated under reflux for 2 hours. Volatile material was then removed in vacuo and the residue was partitioned between chloroform:methanol, 9:1 (100 cm3) and a solution of ethylenediaminetetraacetic acid disodium salt (7 g) in water (100 cm3). The aqueous phase was further extracted with chloroform:methanol, 9:1 (3×100 cm3), and the combined and dried (MgSO4) organic extracts were evaporated to give an oily solid which was triturated with ethyl acetate. Recrystallization of the residue from ethyl acetate-methanol-chloroform afforded the title compound, m.p. 262°-264° (0.359 g).

Provenance & Evidence