N-bromobutanimide → HCID 20337219, compound

HRID 1706174Notes

Reaction equation

HRID 1706174 reaction equation
[CH:1](/[P:4](=[O:9])([O:7][CH3:8])[O:5][CH3:6])=[CH:2]/[CH3:3].[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:6][O:5][P:4](/[CH:1]=[CH:2]/[CH2:3][Br:10])(=[O:9])[O:7][CH3:8]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12530539HCID 12530539, compound

Product 1

HCID 20337219HCID 20337219, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of dimethyl cis-1-propenylphosphonate (6.10 g.) in carbon tetrachloride (60 ml.) was added N-bromosuccinimide (7.97 g.). The reaction mixture was heated to reflux for 2 hours and then cooled to ambient temperature to give precipitates, which were filtered off. The filtrates were concentrated under reduced pressure to give an oily residue, which was subjected to a column chromatography on silica gel and eluted with a mixture of chloroform and ethyl acetate (8:2) to give dimethyl 3-bromo trans-1-propenylphosphonic acid (4.94 g.).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. customto give
  4. customprecipitates
  5. filtrationwhich were filtered off
  6. concentrationThe filtrates were concentrated under reduced pressure
  7. customto give an oily residue, which
  8. washeluted with a mixture of chloroform and ethyl acetate (8:2)

Sources & evidence

ORD record
ord-5782eb1a55b64109bc7c461211d3b40b
Source dataset
uspto-grants-1980_06
Patent number
US04206156

Reaction notes

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