1-Fluoro-3-iodo-5-nitrobenzene → 6-(3-Fluoro-5-nitrophenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

Participants

Reaction Steps

This compound was prepared according to General Method 2 (EXAMPLE 9 ) from Compound 9 (140.2 mg, 0.44 mmol) and 5-fluoro-3-nitroiodobenzene (117.6 mg, 0.44 mmol). The crude material was purified by flash column chromatography (150 ml silica, hexane to 20% acetone/hexane) followed by a second flash column chromatography (100 mL silica, hexane to 20% acetone/hexane) to afford 95 mg (69%) of Compound 280. Data for Compound 280: 1H NMR (400 MHz, acetone-d6) 8.22 (app t, J=3.0, 1.5, 1H), 7.78 (m, 1H), 7.43 (d, J=2.2, 1H), 7.38 (dd, J=8.4, 2.3, 1H), 6.61 (d, J=8.3, 1H), 5.58 (s, 1H), 5.40 (s, 1H), 2.05 (s, 3H), 1.29 (s, 6H).

Provenance & Evidence