Triethyl phosphite → Triethyl 2-fluoro-2-phosphonoacetate

HRID 1033769Notes

Reaction equation

HRID 1033769 reaction equation
[P:1]([O:8][CH2:9][CH3:10])([O:5]CC)[O:2][CH2:3][CH3:4].Br[CH:12]([F:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14]>>[CH2:9]([O:8][P:1]([CH:12]([F:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])([O:2][CH2:3][CH3:4])=[O:5])[CH3:10]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 2733407Acetic acid, 2-bromo-2-fluoro-, ethyl ester

Product 1

HCID 2734865Triethyl 2-fluoro-2-phosphonoacetateYield 77.4%

Conditions

Temperature
150 °C

Procedure

A mixture of 4.00 g (24.0 mmol) of triethyl phosphite and 4.45 g (24.0 mmol) of ethyl bromofluoroacetate (purchased from PCR Inc. Gainesville, Fla.) was heated to 150° C. for 4 h under argon. The contents of the flask were cooled to RT and then distilled under vacuum (0.5 mm Hg) to provide 4.5 g (77%) of title compound as a colorless oil.

Workup

  1. temperatureThe contents of the flask were cooled to RT
  2. distillationdistilled under vacuum (0.5 mm Hg)

Sources & evidence

ORD record
ord-3480beea78234d27a7bca3e804442db1
Source dataset
uspto-grants-1994_05
Patent number
US05312814

Reaction notes

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