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

HRID 949

Reaction equation

HRID 949 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]>>[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

4

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%

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 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%).

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-69bdc7c6a2fb4d4987a431b8e37f7f33
Source dataset
uspto-grants-1998_03
Patent number
US05723470

Linked notes

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