Homoallyl bromide → Diethyl 3-butenylphosphonate

HRID 417171Notes

Reaction equation

HRID 417171 reaction equation
Br[CH2:2][CH2:3][CH:4]=[CH2:5].[P:6]([O:13]CC)([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9]>C(Cl)(Cl)Cl>[CH2:2]([P:6](=[O:13])([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])[CH2:3][CH:4]=[CH2:5]

Participants

4

Reactant 2

HCID 21241Homoallyl bromideHCID 31215Triethyl phosphite

Product 1

HCID 10997850Diethyl 3-butenylphosphonate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-bromo-3-butene (39.0 mmol) and triethyl phosphite (1 g, 6 mmol) were dissolved and reacted in CHCl3 (30 mL). Then, the reaction solution was refluxed for 12 hours, cooled to room temperature and filtered through a glass filter. Chloroform (CHCl3) was completely removed from the solution under vacuum to thereby give an oily compound as the title compound. The 1H NMR results of the compound thus obtained are given as follows.

Workup

  1. temperatureThen, the reaction solution was refluxed for 12 hours
  2. filtrationfiltered through a glass
  3. filtrationfilter
  4. customChloroform (CHCl3) was completely removed from the solution under vacuum

Sources & evidence

ORD record
ord-4a261f2dbf654a348991f1f703983f8c
Source dataset
uspto-grants-2012_01
Patent number
US08089682B2

Reaction notes

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