3-Bromo-5-nitrobenzamide

General procedure: To a suspension of compound 4a (6.9 g, 25.0 mmol) inconcentrated HCl (30 ml) was added SnCl22H2O (20.0 g, 88.0 mmol) in portions. After addition, the mixture was stirred atroom temperature overnight, basified to pH 11 with saturatedNaOH solution and extracted with ethyl acetate (70 ml 4). Thecombined organic phase was washed with brine (100 ml 3), driedover Na2SO4 and concentrated in vacuum to give reduced compound(6.1 g, quantitative) as light-yellow solid. To a solution ofreduced product in pyridine (70 ml) was added 4-fluorophenylsulfonyl chloride (5.4 g, 27.5 mmol) in portions at0 C. Then the mixture was stirred at room temperature overnight.Pyridine was removed under reduced pressure to give a residue, which was solidified by adding H2O (70 ml). The solid was filtered, washed with H2O and dried to give a brown solid, which wasrecrystallized in ethanol to afford 5a (8.6 g, 85.3percent) as white solid.General procedure: 3, 5-dibromobenzoic acid (5g, 17.8 mmol) was suspended in 25 mL of thionyl chloride, an refluxed for 2h. After cooling to room temperature the excess thionyl chloride was removed under reduce pressure and the residue was cautiously poured into 100 mL of ice cold NH4OH 28percent, and stirred at room temperature for 3h. Filtration of the precipitate provide after drying in vacuum the amide intermediate in quantitative yield. The amide was suspended in 25 mL of thionyl chloride, and refluxed for 18h before removing the excess thionyl chloride under reduce pressure. The residue was dissolved in 50 mL of AcOEt, and washed with a saturated solution of NaHCO3 (3 X 50 mL), dry over Na2SO4, and concentrated on a rotary evaporator. Purification of the residue by column chromatography yielded 2.71g (58 percent) 9a as a yellow solid.1H NMR (CDCl3), d = 8.07 (t, 1H, J=2.0 Hz, CHAr); 8.40 (t, 1H, J=2.0 Hz, CHAr); 8.52 (t, 1H, J=2.0 Hz, CHAr). 13C NMR (CDCl3), d = 115.7 (1C, Cq); 115.8 (1C, Cq); 124.3 (1C, Cq); 126.2 (1C, CHAr); 131.3 (1C, CHAr); 140.7 (1C, Cq).

Molecular Weight:245.03
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:243.94835
Monoisotopic Mass:243.94835
Topological Polar Surface Area:88.9
Heavy Atom Count:13
Complexity:228
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes