Triethyl phosphite → 1-(Diethylphosphono)-1-(nonafluorobutyl)undecane

HRID 2416976Notes

Reaction equation

HRID 2416976 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([F:25])([F:24])[C:14]([F:23])([F:22])[C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17].[P:26]([O:33]CC)([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29]>>[CH2:28]([O:27][P:26]([CH:12]([C:13]([F:25])([F:24])[C:14]([F:23])([F:22])[C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH3:2])([O:30][CH2:31][CH3:32])=[O:33])[CH3:29]

Participants

3

Reactant 2

HCID 31215Triethyl phosphite2×HCID 2263051915-Bromo-1,1,1,2,2,3,3,4,4-nonafluoropentadecane

Product 1

HCID 226305081-(Diethylphosphono)-1-(nonafluorobutyl)undecaneYield 94.9%

Conditions

Temperature
150 °C

Procedure

A mixture of 15.03 g of 1-bromo-11-(nonafluorobutyl)undecane and 15.00 g of triethyl phosphite was heated at 150° C. After 18 hr, an additional 9.00 g of triethyl phosphite was added, and heating was continued for 24 hr. Diethyl ethylphosphonate and other volatiles were removed by distillation, b.p. 30-50° C. at 0.05 torr (7 Pa). Bulb-to-bulb distillation of the concentrate provided 16.07 g of 1-(diethylphosphono)-1-(nonafluorobutyl)undecane as a clear, colorless liquid, b.p. 170-200° C. at 0.05 torr (7 Pa).

Workup

  1. temperatureheating
  2. waitwas continued for 24 hr
  3. customDiethyl ethylphosphonate and other volatiles were removed by distillation, b.p. 30-50° C. at 0.05 torr (7 Pa)
  4. distillationBulb-to-bulb distillation of the concentrate

Sources & evidence

ORD record
ord-bf433777a2214835b90811356aab4a24
Source dataset
uspto-grants-2004_11
Patent number
US06824882B2

Reaction notes

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