Phosphoric Acid → HCID 18958202, compound

HRID 1033281Notes

Reaction equation

HRID 1033281 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.[Br:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1.P(=O)(O)(O)O>C1(C)C=CC=CC=1>[Br-:23].[Br:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][P+:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:22])=[CH:2][CH:3]=2)([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)[C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 13956Phosphine, tris(4-methylphenyl)-HCID 685274-Bromobenzyl bromide

Product 1

HCID 18958202HCID 18958202, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
30 °C

Procedure

Into a 50 milliliter glass reactor equipped with a thermometer connected to a temperature controller, a heating mantle, a condenser and a magnetic stirring bar, is charged 5.04 gms (0.0166 mole) of tri-p-tolyl phosphine and 25 gms of toluene. The slurry is heated to 30° C. then 4.6 gms (0.0184 mole) of 4-bromobenzyl bromide is added. This reaction mass is heated to 100° C. and maintained at that temperature for 3.5 hours, then cooled to 29° C. and the resulting phosphonium salt collected by filtration. The salt is washed with 12 gms of toluene then vacuum dried. There is obtained 7.5 gms of catalyst which has a melting point of >250° C. and a chemical shift of 22.1 ppm (phosphoric acid reference).

Workup

  1. customInto a 50 milliliter glass reactor equipped with a thermometer
  2. temperatureThis reaction mass is heated to 100° C.
  3. temperaturemaintained at that temperature for 3.5 hours
  4. temperaturecooled to 29° C.
  5. filtrationthe resulting phosphonium salt collected by filtration
  6. washThe salt is washed with 12 gms of toluene
  7. customvacuum dried
  8. customThere is obtained 7.5 gms of catalyst which

Sources & evidence

ORD record
ord-915d2301302c4479a6da233f0ac59a7b
Source dataset
uspto-grants-1994_05
Patent number
US05310853

Reaction notes

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