Water → Tri-tert-butylphosphonium Tetraphenylborate

HRID 13870

Reaction equation

HRID 13870 reaction equation
[C:1]1([B-:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].O.S(O)(O)(=O)=O.[C:33]([P:37]([C:42]([CH3:45])([CH3:44])[CH3:43])[C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:36])([CH3:35])[CH3:34]>C1(C)C=CC=CC=1>[C:20]1([B-:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1.[C:42]([PH+:37]([C:33]([CH3:36])([CH3:35])[CH3:34])[C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:43])([CH3:44])[CH3:45]

Participants

5

Reactant 3

HCID 962WaterHCID 2723787Sodium Tetraphenylborate2×HCID 86612209Tri-tert-butylphosphine sulfate

Product 1

HCID 23136663Tri-tert-butylphosphonium Tetraphenylborate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A 300-ml four-necked flask was equipped with a stirrer, a thermometer and a reflux condenser. 16.4 g (48 mmol) of sodium tetraphenylborate and 66 ml of water were weighed in the flask, followed by stirring to dissolve sodium tetraphenylborate. While the stirring was continuously carried out, the aqueous solution of tri-tert-butylphosphine sulfate was added to the solution, and the mixture was stirred at 25° C. for 3 hours. After the completion of the reaction, the precipitated product was filtered off. The so obtained crystal was suspended in 100 ml of toluene at 50° C., and the suspension was cooled to 25° C. and filtered. The product filtered off was washed with 100 ml of toluene. The crystal was then suspended in 100 ml of methanol at 50° C., and the suspension was cooled to 25° C. and filtered. The product filtered off was washed with 100 ml of methanol. The crystal obtained was dried to give 19.4 g of objective tri-tert-butylphosphonium tetraphenylborate as white crystal. The yield (mol %) was 93% based on tri-tert-butylphosphine.

Workup

  1. customA 300-ml four-necked flask was equipped with a stirrer
  2. stirringthe mixture was stirred at 25° C. for 3 hours
  3. customAfter the completion of the reaction
  4. filtrationthe precipitated product was filtered off
  5. customThe so obtained crystal
  6. filtrationfiltered
  7. filtrationThe product filtered off
  8. washwas washed with 100 ml of toluene
  9. customwas then suspended in 100 ml of methanol at 50° C.
  10. temperaturethe suspension was cooled to 25° C.
  11. filtrationfiltered
  12. filtrationThe product filtered off
  13. washwas washed with 100 ml of methanol
  14. customThe crystal obtained
  15. customwas dried

Sources & evidence

ORD record
ord-142a14ae4f1c4556968ead328a5c1bc4
Source dataset
uspto-grants-2010_06
Patent number
US07728176B2

Linked notes

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