Ethyl 3-bromo-5-nitrobenzoate

Into a 500-mL round-bottom flask, was placed 3-bromo-5-nitrobenzoic acid (25 g, 101.6 mmol), EtOH (200 mL). This was followed by the addition of SOClThionyl CHLORIDE (15. 7g, 120MOL) was added to a solution of 3-BROMO-5-NITROBENZOIC acid in toluene (100ml). The mixture was REFLUXED for 6 hours. The solvent was evaporated and the residue dissolved in dry tetrahydrofuran (50MUT), ethanol (10MI) was added and the mixture stirred at room temperature for 30 mins. The solvent was evaporated and the residue chromatographed in DICHLOROMETHANE to give the title compound as an off-white solid (13g, 79percent) 1H NMR: (CDCl3) δ 1.44 (3H, t, J=7Hz), 4.45 (2H, q, J=7Hz), 8.48 (1 H, s), 8.54 (1 H, s), 8.78 (1 H, s).Into a 500-mL round-bottom flask purged with and maintained under nitrogen, was placed Into a 500-mL round-bottom flask purged with and maintained under nitrogen, was placed ethyl3-bromo-5-nitrobenzoate (10 g, 36.5 mmol), toluene (250 mL), morpholine (4.6 g, 52.8 mmol), t-BuONa (5 g, 52.0 mmol), Pd2(dba)3CHC13 (1.9 g, 1.93 mmol), BINAP (1.2 g, 1.93 mmol). The resulting solution was stirred for 18 h at 60C and then was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:30 to 1:10). This resulted in 2.8 g (27%) of the title compound as a yellow solid. MS-ESI: 281.1(M+1).Into a 500-mL round-bottom flask purged with and maintained under nitrogen, was placed Into a 500-mL round-bottom flask purged with and maintained under nitrogen, was placed ethyl3-bromo-5-nitrobenzoate (5.5 g, 20.1 mmol), dioxane (250 mL), water(50 mL), (pyridin-4-yl)boronic acid (3.0 g, 24.4 mmol), Cs2CO3 (12.7 g, 38.98 mmol), and Pd(dppf)Cl2 (600 mg, 0.82 mmol). The resulting solution was stirred for 12 h at 90C and then was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:1 to 3:1). This resulted in 4.2 g (77%) of the title compound as a white solid. MS-ESI: 273.1 (M+1).

Molecular Weight:274.07
XLogP3:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:272.96367
Monoisotopic Mass:272.96367
Topological Polar Surface Area:72.1
Heavy Atom Count:15
Complexity:253
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes