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

HRID 1739690Notes

Reaction equation

HRID 1739690 reaction equation
[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]>C(#N)C>[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]

Participants

5

Reactant 2

HCID 31215Triethyl phosphiteHCID 106310791-Propene, 3-bromo-1,1,2-trifluoro-

Product 2

HCID 53986716Diethyl (1,1,2-trifluoro-2-propenyl)phosphonateYield 11%HCID 54339468Diethyl (2,3,3-trifluro-2propenyl)phosphonateYield 14%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2,3,3-trifluoro-2-propenyl bromide (5.25 g, 30 mmol) and triethyl phosphite (4.15 g, 25 mmol) in acetonitrile (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-2propenyl)phosphonate (1.0 g, 14%).

Workup

  1. temperatureat reflux for overnight
  2. customThe residue obtained
  3. customafter evaporation of the solvent
  4. customwas chromatographed over silica gel (hexanes/ethyl acetate/ethanol, 80/20/1)

Sources & evidence

ORD record
ord-55a13c58d28e4ebdafad58ca1ef581fe
Source dataset
uspto-grants-1999_10
Patent number
US05968916

Reaction notes

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