3-BROMO-4-CHLORO-5-NITROPYRIDINE

Step 2. 3-Bromo-4-chloro-5-nitro-pyridine To phosphorous oxychloride (50 ml) cooled in ice was slowly added the product of step 1 (6.57g, 30 mmol). To the resulting stirred solution was added N, N- diethylaniline (4. 77ml, 30 mmol) dropwise. The resulting mixture was warmed to room temperature, then heated to reflux for two hours. After this time the mixture was concentrated under vacuum and the residue poured onto ice. The mixture was extracted into diethyl ether and the organic phase washed twice with water, followed by once with brine before concentrating to a brown oil which solidified on standing, 8. 01g (>100percent)Step 2. 3-Bromo-4-chloro-5-nitro-pyridine To phosphorous oxychloride (50 ml) cooled in ice was slowly added the product of step 1 (6.57g, 30 mmol). To the resulting stirred solution was added N, N- diethylaniline (4. 77ml, 30 mmol) dropwise. The resulting mixture was warmed to room temperature, then heated to reflux for two hours. After this time the mixture was concentrated under vacuum and the residue poured onto ice. The mixture was extracted into diethyl ether and the organic phase washed twice with water, followed by once with brine before concentrating to a brown oil which solidified on standing, 8. 01g (>100percent)To a suspension of 8-b (25 g, 114.16 mol) in toluene (50 mL) was added POClTo a suspension of 17-b (25 g, 114.16 mol) in toluene (50 mL) was added POCIThe product from Step 1 (25.0 g, 114 mmol) was suspended in toluene (50 mL) and POC13 (53 mL, 570 mmol) was added and the slurry was heated to 90 °C overnight. The mixture was cooled and concentrated and the residue was carefully quenched with ice and sat. K2C03 solution then extracted with EtOAc. The organic layers were combined, washed with H20 and brine, dried (MgS04), filtered and concentrated to give the title compound (26.1 g, 97percent) as tan oil which crystallized on standing. MS (ES+) m/e 237, 239 [M+H] +.The product from Step 1 (25.0 g, 114 mmol) was suspended in toluene (50 mL) and POC13 (53 mL, 570 mmol) was added and the slurry was heated to 90 °C overnight. The mixture was cooled and concentrated and the residue was carefully quenched with ice and sat. K2C03 solution then extracted with EtOAc. The organic layers were combined, washed with H20 and brine, dried (MgS04), filtered and concentrated to give the title compound (26.1 g, 97percent) as tan oil which crystallized on standing. MS (ES+) m/e 237, 239 [M+H] +.

Molecular Weight:237.44
XLogP3:2
Hydrogen Bond Acceptor Count:3
Exact Mass:235.89882
Monoisotopic Mass:235.89882
Topological Polar Surface Area:58.7
Heavy Atom Count:11
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes