Triethyl phosphite → 625095-76-3

Temperature

150 °C

A mixture of 5.23 g of 1-bromo-11-(heptadecafluorooctyl)undecane and 4.2 g of triethyl phosphite was heated at 150° C. After 18 hr, diethyl ethylphosphonate and other volatiles were distilled from the reaction mixture, b.p. 30-50° C. at 0.05 torr (7 Pa). The concentrate was combined with an additional 2.0 g of triethyl phosphite, and the mixture was heated at 150° C. After 3 hr, volatiles were again distilled, and the crude 1-diethylphosphono-11-(heptadecafluorooctyl)undecane was dissolved in 10 mL of dichloromethane. To this solution was added 3.1 g of bromotrimethylsilane. After 18 hr at room temperature, the solution was concentrated to a nearly colorless liquid, and the intermediate silylphosphonate ester was dissolved in 200 mL of methanol. The resultant solution was stirred at room temperature for 3 hr and cooled to 0° C. The crude product was collected by filtration, and recrystallization from methanol afforded 2.32 g of 1-phosphono-11-(heptadecafluorooctyl)undecane (CF3(CF2)7 (CH2)11PO3H2) as white crystals, m.p. 115-117° C.

1. distillationdiethyl ethylphosphonate and other volatiles were distilled from the reaction mixture, b.p. 30-50° C. at 0.05 torr (7 Pa)
2. temperaturethe mixture was heated at 150° C
3. waitAfter 3 hr
4. distillationvolatiles were again distilled
5. dissolutionthe crude 1-diethylphosphono-11-(heptadecafluorooctyl)undecane was dissolved in 10 mL of dichloromethane
6. additionTo this solution was added 3.1 g of bromotrimethylsilane
7. waitAfter 18 hr at room temperature
8. concentrationthe solution was concentrated to a nearly colorless liquid
9. dissolutionthe intermediate silylphosphonate ester was dissolved in 200 mL of methanol
10. temperaturecooled to 0° C
11. filtrationThe crude product was collected by filtration, and recrystallization from methanol

ORD record

ord-8d0eb1b16c3f42bbabb1cc4f9b2e9938

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06824882B2