Triethyl 2-fluoro-2-phosphonoacetate

Chemical Properties

clear colorless liquid

Uses

Reactant for:

• Diels-Alder reactions
• Biosynthesis of terpene
• Stereoselective synthesis of unsaturated esters, fluorides and nitriles from the reactions of aldehydes and ketones using Wadsworth-Emmons phosphonates
• Synthesis of quinolones
• Horner-Wadsworth-Emmons asymmetric hydration
• Addition reactions and the subsequent application to click chemistry
• Asymmetric intermolecular Stetter reactions

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 4730, 1995 DOI: 10.1021/jo00120a014

reaction suitability

reaction type: C-C Bond Formation

Synthesis

Ethyl 2-bromo-2-fluoroacetate (5.0 g, 27 mmol) was mixed with triethyl phosphite (13 mL) and the reaction was heated at 130°C for 23 hours. After completion of the reaction, the resulting mixture was distilled under reduced pressure (1.4 mbar, 75-110°C) to afford triethyl 2-fluoro-2-phosphonoacetate, the product being a pale yellow oil (6.0 g, 92% yield).

References

[1] Phosphorus, Sulfur and Silicon and Related Elements, 2000, vol. 160, p. 195 - 205
[2] Patent: WO2017/100668, 2017, A1. Location in patent: Page/Page column 162
[3] Patent: WO2018/103058, 2018, A1. Location in patent: Page/Page column 161; 165-166; 339
[4] Journal of the American Chemical Society, 2007, vol. 129, # 15, p. 4536 - 4537
[5] Heterocycles, 2004, vol. 63, # 3, p. 699 - 706