2-Iodotoluene → HCID 12722692, compound

Temperature

160 °C

A mixture of o-iodotoluene and anhydrous nickel chloride is stirred under a nitrogen atmosphere at 160° C. While maintaining the temperature in a range of 160°-170° C., diethylmethylphosphonite is added dropwise to the mixture. Ethyliodide distills rapidly from the mixture. Following the addition of the phosphonite, the reaction mixture is heated at 165°-175° C., for an hour, then cooled. Upon cooling, the reaction mixture is poured onto ice-water and extracted with chloroform. The chloroform extracts are washed with water, dried over magnesium sulfate and then concentrated in vacuo to yield a colorless oil. This oil is treated directly with a solution containing phosphorous pentachloride in benzene and the resulting mixture is refluxed for 1 hour, then concentrated in vacuo to yield an oil. This oil is distilled to yield methyl-o-tolylphosphinyl chloride. The methyl-o-tolylphosphinyl chloride is added to a liter of carbon tetrachloride and the resulting mixture is heated to reflux temperatures by irradiating the mixture using a 275 watt sunlamp mounted below the pyrex glass flask. Chlorine gas is bubbled into the reaction vessel until formation of o-chloromethylphenylmethylphosphinyl chloride is 60-75% complete in order to prevent formation of the dichloro derivative. The irradiation is then stopped and the reaction mixture is concentrated in vacuo to yield an oily residue. The oily residue is fractionally distilled to remove any unreacted methyl-o-tolylphosphinyl chloride to yield o-chloromethylphenylmethylphosphinyl chloride.

1. additionis added dropwise to the mixture
2. distillationEthyliodide distills rapidly from the mixture
3. additionthe addition of the phosphonite
4. temperaturethe reaction mixture is heated at 165°-175° C., for an hour
5. temperaturecooled
6. temperatureUpon cooling
7. additionthe reaction mixture is poured onto ice-water
8. extractionextracted with chloroform
9. washThe chloroform extracts are washed with water
10. dry with materialdried over magnesium sulfate
11. concentrationconcentrated in vacuo
12. customto yield a colorless oil
13. additionThis oil is treated directly with a solution
14. temperaturethe resulting mixture is refluxed for 1 hour
15. concentrationconcentrated in vacuo
16. customto yield an oil
17. distillationThis oil is distilled

ORD record

ord-d28b8e7c46b840d58d04ca7425969e25

Source dataset

uspto-grants-1981_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04272278