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6-(5-Fluoro-3-nitrophenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 280, structure 4 of Scheme II, where R1 =5-fluoro-3-nitrophenyl) 1-Fluoro-3-nitroiodobenzene To a 25 mL round-bottom flask equivuipped with a magnetic stir bar 3-iodo-5-nitroaniline (543.3 mg, 2.06 mmol) and methylene chloride (10 mL) were added under nitrogen. Nitrogen was bubbled through the colorless solution for 15 min. The solution was cooled to 0° C. in an ice bath. At that point approximately 500 mg nitrosonium tetrafluoroborate was added in one portion making a cloudy precipitate. The reaction was allowed to continue stirring for 2 hours. The mixture was kept under nitrogen as 10 mL dry, deoxygenated ortho-dichlorobenzene was added. A distillation apparatus was fitted to the reaction flask. The flask was placed in an oil bath and was heated until the material had completely distilled over. The crude product was isolated by washing the residue through a short column (74 mL silica, hexane). Purification by silica gel chromatography (74 mL silica, hexane) afforded 279.4 mg (50%) of 5-fluoro-3-nitroiodobenzene. Data for 5-fluoro-3-nitroiodobenzene: 1H NMR (400 MHz, acetone-d6) 8.36 (s, 1 H), 8.00 (m, 2 H).

1. customNitrogen was bubbled through the colorless solution for 15 min
2. additionAt that point approximately 500 mg nitrosonium tetrafluoroborate was added in one portion
3. customdry
4. customdeoxygenated ortho-dichlorobenzene
5. additionwas added
6. customA distillation apparatus was fitted to the reaction flask
7. customThe flask was placed in an oil bath
8. temperaturewas heated until the material
9. distillationhad completely distilled over
10. customThe crude product was isolated
11. washby washing the residue through a short column (74 mL silica, hexane)
12. customPurification by silica gel chromatography (74 mL silica, hexane)