Ethyl Bromide → HCID 19438174, compound

HRID 2379251Notes

Reaction equation

HRID 2379251 reaction equation
[C:1]1([CH3:22])[CH:6]=[CH:5][C:4]([P:7]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[CH2:23]([Br:25])[CH3:24]>C1(C)C(C)=CC=CC=1>[Br-:25].[CH2:23]([P+:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:22])=[CH:2][CH:3]=1)([C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1)[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)[CH3:24]

Participants

4

Reactant 2

HCID 6332Ethyl Bromide3×HCID 13956Phosphine, tris(4-methylphenyl)-

Product 1

HCID 19438174HCID 19438174, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
32 °C

Procedure

Into a 1 liter glass reactor equipped with a thermometer connected to a temperature controller, a heating mantle, a condenser and a magnetic stirring bar, are charged 250 gms (0.822 mole) of tri-p-tolylphosphine and 600 gms of xylene. The slurry is heated to 32° C., then 117 gms (1.073 mole) of ethyl bromide is added. This reaction mass is maintained at 32° C. for 1.5 hours, then heated to 45° C. and maintained at that temperature for 21 hrs, then heated to 65° C. and maintained at that temperature for 2 hours, then heated to 90° C. and maintained at that temperature for 2 hours. This mixture is cooled to 32° C., then 43.9 gms of ethyl bromide is added and mixed for 1 hour, then heated to 45° C. and maintained at that temperature for 18 hours, then cooled to 33° C. and an additional 15.7 gms of ethyl bromide is added and the temperature is maintained for 1 hour. The reaction mass is then heated to 45° C. and maintained at that temperature for 2 hours. The reaction material is then cooled to 50° C. and filtered. The solid phosphonium salt is washed with 200 gms of xylene resulting in 220 gms of clean phosphonium salt. The phosphonium salt has a melting point of 222°-224° C.

Workup

  1. customInto a 1 liter glass reactor equipped with a thermometer
  2. temperatureThis reaction mass is maintained at 32° C. for 1.5 hours
  3. temperatureheated to 45° C.
  4. temperaturemaintained at that temperature for 21 hrs
  5. temperatureheated to 65° C.
  6. temperaturemaintained at that temperature for 2 hours
  7. temperatureheated to 90° C.
  8. temperaturemaintained at that temperature for 2 hours
  9. temperatureThis mixture is cooled to 32° C.
  10. additionmixed for 1 hour
  11. temperatureheated to 45° C.
  12. temperaturemaintained at that temperature for 18 hours
  13. temperaturecooled to 33° C.
  14. temperaturethe temperature is maintained for 1 hour
  15. temperatureThe reaction mass is then heated to 45° C.
  16. temperaturemaintained at that temperature for 2 hours
  17. temperatureThe reaction material is then cooled to 50° C.
  18. filtrationfiltered
  19. washThe solid phosphonium salt is washed with 200 gms of xylene resulting in 220 gms of clean phosphonium salt

Sources & evidence

ORD record
ord-dd8c8e09f875400ca72cebcb19efba98
Source dataset
uspto-grants-1994_11
Patent number
US05360886

Reaction notes

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