Phosphine → 2,6-bis(2,4-Dimethylphenyl)-4-Phenylphosphabenzene

HRID 1635714Notes

Reaction equation

HRID 1635714 reaction equation
F[B-](F)(F)F.[CH3:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[C:14]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[C:16]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][C:27]=2[CH3:33])[O+]=1.[PH3:34]>C(O)CCC>[CH3:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[C:14]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[C:16]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][C:27]=2[CH3:33])[P:34]=1

Participants

4

Reactant 2

HCID 24404PhosphineHCID 11374391HCID 11374391, compound

Product 1

HCID 114858072,6-bis(2,4-Dimethylphenyl)-4-Phenylphosphabenzene

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

20 g (44 mmol) of 2,6-bis(2,4-dimethylphenyl)-4-phenylpyrylium tetrafluoroborate in 150 ml of n-butanol were used as starting material. The autoclave product obtained after the reaction with PH3 was evaporated to half its volume under reduced pressure. The solid which precipitated was filtered off with suction, washed with n-butanol and subsequently dissolved in toluene. The toluene solution was then washed with water until the aqueous phase was neutral. After removal of the solvent and washing with a little n-pentane, the residue was dissolved in 250 ml of diethyl ether/methanol (3:2). The solution obtained was evaporated under reduced pressure at about 30° C. until a solid precipitated. The solid was filtered off with suction, washed with a little methanol and n-pentane and subsequently dried in a high vacuum. Yield: 8.9 g (53%) of white solid.

Workup

  1. customThe autoclave product obtained
  2. customwas evaporated to half its volume under reduced pressure
  3. customThe solid which precipitated
  4. filtrationwas filtered off with suction
  5. washwashed with n-butanol
  6. dissolutionsubsequently dissolved in toluene
  7. washThe toluene solution was then washed with water until the aqueous phase
  8. customAfter removal of the solvent
  9. washwashing with a little n-pentane
  10. dissolutionthe residue was dissolved in 250 ml of diethyl ether/methanol (3:2)
  11. customThe solution obtained
  12. customwas evaporated under reduced pressure at about 30° C. until a solid
  13. customprecipitated
  14. filtrationThe solid was filtered off with suction
  15. washwashed with a little methanol and n-pentane
  16. customsubsequently dried in a high vacuum

Sources & evidence

ORD record
ord-798e041424694b9daddafc1c1a29016c
Source dataset
uspto-grants-2003_01
Patent number
US06509505B1

Reaction notes

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