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

HRID 1779357Notes

Reaction equation

HRID 1779357 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-trifluoro-2-propenyl)phosphonate (0.8 g, 11%) and diethyl (2,3,3-trifluoro-2-propenyl)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-74a3a865e2264160a27c8010e0b71b94
Source dataset
uspto-grants-1997_05
Patent number
US05627174

Reaction notes

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