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

HRID 439678Notes

Reaction equation

HRID 439678 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-e2f1c2acf1374598be75fb15eefeb289
Source dataset
uspto-grants-1996_05
Patent number
US05514717

Reaction notes

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