Triphenylphosphine → (3-Ethoxy-3-oxopropyl)(triphenyl)phosphanium bromide

HRID 1242272Notes

Reaction equation

HRID 1242272 reaction equation
[Br:1][CH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:9]1([P:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[Br-:1].[CH2:7]([O:6][C:4]([CH2:3][CH2:2][P+:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5])[CH3:8]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 68320Ethyl 3-bromopropionate

Product 1

HCID 2773637(3-Ethoxy-3-oxopropyl)(triphenyl)phosphanium bromideYield 18%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 3-bromopropionate (1.81 g, 0.01 moles) was added to a three-necked, 100 mL round bottom flask equipped with a magnetic stirrer, thermocouple and temperature controller, condenser, and heating mantle. Triphenylphosphine (2.62 g, 0.01 moles) and toluene (25 ml) was added and the mixture was heated to reflux temperature. As the temperature turned 90° C., the mixture turned slightly cloudy. After 3 hours at 115° C., the reaction mixture was cooled to room temperature, during which time a yellow colored waxy material settled to the bottom of the reaction flask. The liquid was removed and the residual waxy solid dissolved in dichloromethane (about 10 ml). Diethyl ether (about 15 ml) was added to the dichloromethane solution and a precipitate was formed. The precipitate was collected by filtration and dried under vacuum to give the required phosphonium salt (0.8 grams; 18% yield). The structure of the product was confirmed by 1H NMR analysis.

Workup

  1. customequipped with a magnetic stirrer
  2. temperaturethermocouple and temperature controller, condenser, and heating mantle
  3. temperaturethe mixture was heated
  4. temperatureto reflux temperature
  5. customturned 90° C.
  6. customThe liquid was removed
  7. dissolutionthe residual waxy solid dissolved in dichloromethane (about 10 ml)
  8. additionDiethyl ether (about 15 ml) was added to the dichloromethane solution
  9. customa precipitate was formed
  10. filtrationThe precipitate was collected by filtration
  11. customdried under vacuum

Sources & evidence

ORD record
ord-436ece98e62b4559a05341000bbef2a5
Source dataset
uspto-grants-2006_10
Patent number
US07115676B2

Reaction notes

Loading…