Ethyl 4,4,4-trifluoroacetoacetate → HCID 18416189, compound

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Reaction Steps

This compound was prepared according to General Method 11 (EXAMPLE 22) from 4-bromo-3-chloroaniline (2.06 g, 10.0 mmol), ethyl 4,4,4-trifluoroacetoacetate (2.30 g, 12.5 mmol) in 50 mL toluene followed by heating in 33 mL conc. H2SO4 to afford 2.08 g (64%) of 6-bromo-7-chloro-4-(trifluoromethyl)-quinolin-2(1H)-one, an off-white solid. This material was converted to the corresponding imino ether according to General Method 12 (EXAMPLE 22) with isopropyl iodide (4.32 g, 25.4 mmol) and CsF (3.85 g, 25.4 mmol) in 32 mL DMF to afford 1.34 g (57%) of 6-bromo-7-chloro-2-isopropoxy-4-(trifluoromethyl)quinoline, a white solid, after flash chromatography (hexanes). Data for 6-bromo-7-chloro-2-isopropoxy-4-(trifluoromethyl)quinoline: 1H NMR (400 MHz, CDCl3) δ 8.22 (broad s, 1H), 8.00 (s, 1H), 7.17 (s, 1H), 5.51 (hept, 1H, J=6.2), 1.40 (d, 6H, J=6.2).

Provenance & Evidence