1-Fluoro-4-iodo-2-nitrobenzene

Intermediate Example 3.1 -Fluoro-4-iodo-2-nitrobenzene To a solution of l-fluoro-2-nitrobenzene (5 g, 35.43 mmol) in triflic acid (15.6 ml, 177.15 mmol, 5 eq.) at 0 °C was added N-iodosuccinimide (9.57 g, 42.5 mmol, 1.2 eq.) portionwise and the mixture was stirred at RT for 1 h. The mixture was quenched by the addition of water and extracted with diethylether (3 To a solution of 1-fluoro-2-nitrobenzene (5 g, 35.43 mmol) in triflic acid (15.6 ml, 177.15 mmol, 5 eq.) at 0° C. was added N-iodosuccinimide (9.57 g, 42.5 mmol, 1.2 eq.) portionwise and the mixture was stirred at RT for 1 h. Add isoamyl nitrite (18. 6 g, 160 mmol) to a suspension of 4-fluoro-3- nitrophenylamine (5. 0 g, 32 mmol) in diiodomethane (150 mL). Stir under nitrogen at room temperature for 1 h. Heat at 70 °C for 1 h. Cool to room temperature and concentrate. Dilute with dichloromethane (500 mL) and water (100 mL). Collect the organic, concentrate and purify (silica gel chromatography, eluting with a gradient of 100 : 0 to 80 : 20 hexanes : ethyl acetate), to give the title compound as a yellow oil (1. 22 g, 14percent). 1H NMR (300 MHz, CDC13) 6 7. 02-7. 11 (m, 1H), 7. 89-7. 97 (m, 1H), 8. 32-8. 39 (dd, J = 2. 2 Hz, 6. 9 Hz, 1H).General procedure: A mixture of benzenesulfonamides (1, 1.0 mmol), halogenated nitrobenzene(2, 1.0 mmol) and K2CO3 (1.1 mmol) were dissolved in DMF in a microwave tube. Then, the reaction mixture was irradiated in a microwave apparatus at 140 C for 12 minutes. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by column chromatography on silica gel to the desired products 3.

Molecular Weight:267.00
XLogP3:2.5
Hydrogen Bond Acceptor Count:3
Exact Mass:266.91925
Monoisotopic Mass:266.91925
Topological Polar Surface Area:45.8
Heavy Atom Count:11
Complexity:161
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes