Anisole → HCID 22647916, compound

Participants

Reaction Steps

A solution of 1-(2,6-dichlorophenyl)-3-(4-methoxyphenyl)methyl-5-bromo-7-methoxy-3,4-dihydro-2(1H)-quinazolinone (30.91 g, 0.0592 mol) (INTERMEDIATE 22) and anisole (28 ml, 0.258 mol) in 350 mL trifluoroacetic acid under a nitrogen atmosphere was refluxed for 2 h. The solution was cooled to RT and concentrated. The residue was partitioned between 500 mL NaHCO3 and 500 mL EtOAc. The organic phase was washed with water (500 mL) and brine (500 mL) and concentrated. The NaHCO3 and brine phases contained a suspension of precipitated product. This material was collected by filtration and combined with the crude. The combined crude was suspended in ethyl ether, filtered and washed with ethyl ether and hexanes to give 1-(2,6-dichlorophenyl)-5-bromo-7-methoxy-3,4-dihydro-2(1H)-quinazolinone. 1H NMR(CDCl3, 500 MHz): δ 3.68 (s, 3H), 4.64 (s, 2H), 5.46 (s, 1H), 5.62 (d, 1H, J=2.3 Hz), 6.79 (d, 1H, J=2.5 Hz), 7.36 (t, 1H, J=8.1 Hz), 7.50 (d, 2H, J=8.2 Hz). MS(ES) 401 (M+1); LC 1: 3.18 min.

Provenance & Evidence