Glycerol → 3-[(3,5-Dichloro-6-fluoropyridin-2-yl)oxy]propane-1,2-diol

To a solution of 12.9 grams (0.07 mole) of 3,5-dichloro-2,6-difluoropyridine in 50 milliliters of glycerol was added over an 8 minute period 2.9 grams of sodium hydroxide in 25 milliliters of glycerol. The mixture was maintained at ~85° C. for ~17 minutes, cooled and poured into 200 milliliters of cold water. The solid which precipitated was air dried and taken up in benzene, dried and most of the benzene was removed by evaporation under reduced pressure. The residue was mixed with hexane and cooled and the crystalline 3-(3,5-dichloro-6-fluoro-2-pyridyloxy)-1,2-propanediol product which precipitated was recovered by filtration. The product was covered in a yield of 10 grams (56 percent of theoretical). The product melted at 78°-80° C. and was found upon analysis to have carbon, hydrogen, chlorine and nitrogen contents of 37.5, 2.9, 27.6 and 5.6 percent, respectively, as compared with the theoretical contents of 37.5, 3.2, 27.7 and 5.5 percent, calculated for the above-named compound.

1. temperatureThe mixture was maintained at ~85° C. for ~17 minutes
2. temperaturecooled
3. customThe solid which precipitated
4. customdried
5. dry with materialdried and most of the benzene
6. customwas removed by evaporation under reduced pressure
7. additionThe residue was mixed with hexane
8. temperaturecooled
9. customthe crystalline 3-(3,5-dichloro-6-fluoro-2-pyridyloxy)-1,2-propanediol product which precipitated
10. filtrationwas recovered by filtration

ORDレコード

ord-930c26dbf8734719b9a562d20516bc9e

出典データセット

uspto-grants-1979_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04180395