2,3-Dichloro-5-(trichloromethyl)pyridine

Liquid

of Nicotinic acid to 2, 3-dichloro-5-(trichloromethyl)pyridine. Nicotinic acid (50 g, 0.4 mole) and phosphorous trichloride (223 g, 1.6 mole) were added to an 0.5 L jacketed autoclave, connected to a cooling- heating circulator. The temperature of the reaction mixture was adjusted to 120 °C and chlorine gas (115 g, 1.6 mole) was added to head space from a pressure bottle. During addition of chlorine was the temperature maintained between 120 °C and 140 °C with cooling circulation on the jacket. After addition of chlorine gas is the pressure in the autoclave around 3 bar. The temperature is increased to 180 °C (will be preferred to increase to 210 °C, but this was not possible in the current setup) and kept there for 144 hours (210 °C will finish reaction in 16 hours). During the reaction HCl(g) was removed through a scrubber periodically to keep pressure between 12 and 16 bar. The autoclave was then cooled to 25 °C and ventilated to a Caustic Lye scrubber. The resulting solution was heated to reflux to recover phosphorous trichloride by distillation. The autoclave was closed again and chlorine gas (50 g, 0.5 mole) was added at room temperature. The resulting mixture was heated to 130 °C and pressure was kept below 15 bar by removing HCl(g) above a condenser to a caustic lye scrubber. When pressure becomes stable (typically after 2 - 4 hours), the reaction is considered completed and the autoclave cooled down. If analysis shows otherwise, the final chlorination procedure can be repeated. The reaction mixture was then transferred to a round bottomed flask and phosphoryl chloride was removed by distillation. In case there is any solid PC1The obtained 2-chloro-5-trichloromethylpyridine 46.2 g, After adding the catalyst, the temperature is raised to 150-160°C.Slowly dry the chlorine gas for heavy chlorination.After 6 hours of reaction, dilute the reaction solution with benzene, wash with water and dry the organic phase.After evaporating the benzene under reduced pressure, After distillation, 50.3 g of oily product was obtained.That is the intermediate 2, 3-dichloro-5-trichloromethylpyridine, The yield was 90percent and the content was 95percent.EXAMPLE 7 Conversion of Nicotinic acid to a mixture of 2-chloro-5- (trichloromethyl)pyridine and 2, 3-dichloro-5-(trichloromethyl)pyridine. To a 250 ml Berghof autoclave with PTFE lining was added Nicotinic acid (20g, 162 mmole) and phosphorous pentachloride (139 g, 668 mmole). The autoclave was closed and heated to 210 °C for 14 hours. During the heating an exotherm was observed around a temperature of 130 °C bringing the temperature to 190 °C and a pressure increase from 2 bar to 8 bar within 2 minutes. The heating was continued to 210 °C. After the 14 hours the pressure had increased to 37 Bar. The autoclave was cooled to room temperature, ventilated to a scrubber, opened and quantified by GC indicating a yield of 2- chloro-5-(trichloromethyl)pyridine of 33percent compared to the Nicotinic acid starting material and a yield of 2, 3-dichloro-5-(trichloromethyl)pyridine 60percent.500 g (3.08 mol) of 2-chloro-5-chloromethylpyridine (molecular weight: 162 g / mol) and 50 g (10percent by weight) of copper oxide were charged into a 1 L four-necked flask equipped with a thermometer, a condenser and a mechanical stir And heated to 275 ° C, and then chlorinated by passing Cl 2 into the above solution, and the reaction was carried out for 60 hours to obtain 562 g (2.12 mol) of 2, 3-dichloro-5-trichloromethylpyridine. A solution of 562 g (2.12 mol) of 2, 3-dichloro-5-trichloromethylpyridine was heated to 70 ° C and added with 5 g of catalyst antimony pentachloride followed by 210 g (10.5 mol) of hydrogen fluoride at 200 ° C, 8.5 MPa pressure for 30 hours to give 421 g (1.95 mol) of 2, 3-dichloro-5-trifluoromethylpyridine in a yield of 63.2percent from 2-chloro-5-chloromethylpyridine,

Intermediates

Molecular Weight:265.3
XLogP3:4.1
Hydrogen Bond Acceptor Count:1
Exact Mass:264.860037
Monoisotopic Mass:262.862988
Topological Polar Surface Area:12.9
Heavy Atom Count:12
Complexity:157
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes