2-Bromo-3-nitropyridine

Off-white to cream crystalline powder

A solution of 48percent aq. HBr (3.60 mL, 32.0 mmol) dissolved in DMSO (35 mL) was added dropwise to a solution of 3-nitropyridine-2-amine 10, (1.0 g, 7.19 mmol) in a mixture of 35 mL of DMSO, KNOA solution of 48% aq. HBr (3.60 mL, 32.0 mmol) dissolved in DMSO (35 mL) was added dropwise to a solution of 3-nitropyridine-2-amine 10, (1.0 g, 7.19 mmol) in a mixture of 35 mL of DMSO, KNO2 (2.45 g, 28.75 mmol) and CuBr (0.206 g, 1.44 mmol) at 35 C with stirring. The added mixture was stirred at 35 C for 4 h and then transferred to a solution of K2CO3 (7 g) in 100 mL of ice water. The reaction mixture was then taken up in diethyl ether, and the ethereal extracts were washed with water and dried over anhydrous Na2SO4. Removal of the solvent under reduced pressure gave the crude product. The crude product was purified by silica gel chromatography (eluent: 100% dichloromethane) to give 2-bromo-3-nitropyridine 11 as a beige powder (0.662 g, 45%). Rf = 0.75 (dichloromethane); mp 121-122 C (lit. [12] : 123-124 C); IR (KBr) numax (cm-1): 3042 (nuCHar), 1578 and 1562 (nuC=C), 1524 (nuasNO2), 1350 (nusy NO2); 1H NMR (400 MHz, DMSO-d6): delta 8.73 (dd, 1H, J1 = 1.6 Hz, J2 = 4.8 Hz, H-6), 8.54 (dd, 1H, J1 = 1.6 Hz, J3 = 8.0 Hz, H-4), 7.79 (dd, 1H, J2 = 4.8 Hz, J3 = 8.0 Hz, H-5); 13C NMR (100 MHz, DMSO-d6): delta 153.26 (C-6), 147.08 (C-3), 134.48 (C-4), 132.08 (C-2), 124.44 (C-5); MS (ESI) m/z (%): 202.9 (100) [M + H]+, 204.9 (100) [M + H + 2]+. Anal. calcd for C5H3BrN2O2: C, 29.58; H, 1.49; N, 13.80. Found: C, 29.63; H, 1.50; N, 13.83.In a reaction flask, 35.4 g (100 mmol) of 2-borate-triphenylene, 135 g of A-2, 167 g of B-2, and 2 liters of DMF were added to the reaction flask and stirred under nitrogen.Sodium tert-butoxide was added for 20 minutes, and the reaction was refluxed at elevated temperature for 24 hours.No material was present on the plate, and the reaction was stopped to obtain a red-black solution.After cooling to room temperature, it was poured into water to precipitate a large amount of blood red solid.The solid was washed with petroleum ether and ethyl acetate 1:1 to give 261 g of a red solid.

Molecular Weight:202.99
XLogP3:1.7
Hydrogen Bond Acceptor Count:3
Exact Mass:201.93779
Monoisotopic Mass:201.93779
Topological Polar Surface Area:58.7
Heavy Atom Count:10
Complexity:136
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes