Phenethyl bromide → HCID 13274713, compound

HRID 1262623Notes

Reaction equation

HRID 1262623 reaction equation
[Mg].Br[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl[P:12]([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]>CCOCC>[C:5]1([CH2:4][CH2:3][P:12]([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 68530Ethyl phosphorochloriditeHCID 5462224Magnesium

Product 1

HCID 13274713HCID 13274713, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A suspension of 4.13 g (0.172 mol) of magnesium in 45 ml of dry ether under argon was treated with a solution of 31.2 g (0.168 mol) of 1-bromo-2-phenylethane (Aldrich) in 90 ml of dry ether, added at a rate that maintained reflux. The reaction was stirred overnight at room temperature under argon, then filtered under argon, cooled to 10° C. and treated with 26.3 g (0.168 mol) of diethyl chlorophosphonite (Aldrich) dissolved in 60 ml of dry ether, added slowly to keep the temperature near 10° C. After addition, the reaction was refluxed for 1 hour, filtered under argon and distilled at 1 atm to remove ether. Vacuum distillation of the residue gave 20.6 g (54%) of the title A compound which distilled at 94°-96° C./0.55 mm Hg. The 1H-NMR and 13C-NMR of this material were both consistent with the assigned structure.

Workup

  1. additionadded at a rate that
  2. temperaturemaintained
  3. temperaturereflux
  4. filtrationfiltered under argon
  5. temperaturecooled to 10° C.
  6. additionadded slowly
  7. customnear 10° C
  8. additionAfter addition
  9. temperaturethe reaction was refluxed for 1 hour
  10. filtrationfiltered under argon
  11. distillationdistilled at 1 atm
  12. customto remove ether
  13. distillationVacuum distillation of the residue
  14. customgave 20.6 g (54%) of the title A compound which
  15. distillationdistilled at 94°-96° C./0.55 mm Hg

Sources & evidence

ORD record
ord-9831d685cc3342e591d768e665276ee5
Source dataset
uspto-grants-1984_06
Patent number
US04452791

Reaction notes

Loading…