Iodine → 2,4-Dichloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazine

温度

-78 °C

Alternatively, to a mixture of magnesium (1.46 g, 60.0 mmol) and tetrahydrofuran (100 ml) was added a small crystal of iodine followed by 4-chloro-2-iodo-toluene (12.62 g, 50 mmol). The mixture was heated under gentle reflux in an argon atmosphere for 6 hours and then cooled to −78° C. A solution of cyanuric chloride (7.84 g, 42.5 mmol) in tetrahydrofuran (45 ml) was added over 25 minutes. After stirring at −78° C. for 1 hour, the mixture was slowly warmed to room temperature and stirred for 16 hours. The reaction mixture, cooled in an ice bath, was quenched by slow addition of hydrochloric acid (1 M, 15 ml). The mixture was diluted with water (150 ml) and extracted with dichloromethane (3×125 ml). The combined extracts was washed with water (150 ml), dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (7:93) to provide 2,4-dichloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazine (10.2 g, 87% yield) as a white powder.

1. temperatureThe mixture was heated
2. temperatureunder gentle reflux in an argon atmosphere for 6 hours
3. temperaturethe mixture was slowly warmed to room temperature
4. stirringstirred for 16 hours
5. temperatureThe reaction mixture, cooled in an ice bath
6. customwas quenched by slow addition of hydrochloric acid (1 M, 15 ml)
7. additionThe mixture was diluted with water (150 ml)
8. extractionextracted with dichloromethane (3×125 ml)
9. washThe combined extracts was washed with water (150 ml)
10. dry with materialdried over sodium sulfate
11. concentrationconcentrated under reduced pressure
12. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (7:93)

ORDレコード

ord-70e2a9c8b57443fdab1a8176417c65a1

出典データセット

uspto-grants-2007_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07291616B2