Benzoyl Peroxide → Diethyl [(1E)-3-bromoprop-1-en-1-yl]phosphonate

HRID 2051962Notes

Reaction equation

HRID 2051962 reaction equation
[CH:1](/[P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])=[CH:2]\[CH3:3].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:3]/[CH:2]=[CH:1]/[P:4](=[O:11])([O:5][CH2:6][CH3:7])[O:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5702572Diethyl (1E)-prop-1-en-1-ylphosphonate

Product 1

HCID 5702525Diethyl [(1E)-3-bromoprop-1-en-1-yl]phosphonateYield 58.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of diethyl trans-1-propenylphosphonate (32.04 g.) in carbon tetrachloride (320 ml.) were added N-bromosuccinimide (41.65 g.) and dibenzoylperoxide (2.8 g.). The reaction mixture was heated to reflux for 1.5 hours and stirred for 30 minutes under ice-cooling. Insoluble materials were removed off by filtration and the filtrate was concentrated under reduced pressure to give an oily residue (63.09 g.), which was subjected to a column chromatography on silicagel and eluted with chloroform. The eluates were evaporated to dryness under reduced pressure to give an oily diethyl 3-bromo-trans-1-propenylphosphonate (27.04 g.).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. temperaturecooling
  4. customInsoluble materials were removed off by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto give an oily residue (63.09 g.), which
  7. washeluted with chloroform
  8. customThe eluates were evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9363f1fddaf74e7e887f8ec6a2a96546
Source dataset
uspto-grants-1980_01
Patent number
US04182758

Reaction notes

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