Triethyl phosphite → Diethyl (2,3,3-trifluro-2propenyl)phosphonate

Reaktionsgleichung

[F:1][C:2](=[C:5]([F:7])[F:6])[CH2:3]Br.[P:8]([O:15][CH2:16][CH3:17])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11]>>[F:6][C:5]([P:8](=[O:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])([F:7])[C:2]([F:1])=[CH2:3].[F:1][C:2](=[C:5]([F:7])[F:6])[CH2:3][P:8](=[O:9])([O:12][CH2:13][CH3:14])[O:15][CH2:16][CH3:17]

Komponenten

Edukt 2

HCID 31215Triethyl phosphite

HCID 106310791-Propene, 3-bromo-1,1,2-trifluoro-

Produkt 2

HCID 53986716Diethyl (1,1,2-trifluoro-2-propenyl)phosphonateAusbeute 11 %

HCID 54339468Diethyl (2,3,3-trifluro-2propenyl)phosphonateAusbeute 14 %

Versuchsvorschrift

A solution of 2,3,3-trifluoro-2-propenyl bromide (5.25 g, 30 mmol) and triethyl phosphite (4.15 g, 25 mmol) in acetonltrile (15 mL) was heated at reflux for overnight. The residue obtained after evaporation of the solvent was chromatographed over silica gel (hexanes/ethyl acetate/ethanol, 80/20/1) to give diethyl (1,1,2-trifluro-2-propenyl)phosphonate (0.8 g, 11%) and diethyl (2,3,3-trifluro-2-propenyl)phosphonate (1.0 g, 14%).