Water → Cyclohexylisopropylphenylphosphine

HRID 979712Notes

Reaction equation

HRID 979712 reaction equation
[CH:1]1([Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]1([P:15](Cl)Cl)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH:18]([Mg]Br)([CH3:20])[CH3:19].O>CCOCC>[CH:1]1([P:15]([CH:18]([CH3:20])[CH3:19])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 12573Phenyl phosphorus dichlorideHCID 178418365HCID 178418365, compoundHCID 178478990HCID 178478990, compound

Product 1

HCID 54482329CyclohexylisopropylphenylphosphineYield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-25 °C

Procedure

A Grignard mixture of 55 mmoles of cyclohexylmagnesium chloride (prepared from 1.5 g of magnesium turnings and 6.5 g of cyclohexylchloride in 20 ml of anhydrous ether) was added dropwise to a stirred solution of 8.9 g (50 mmoles) of phenyldichlorophosphine in 50 ml of anhydrous ether maintained under an inert atmosphere at -25° C. After the addition was complete, the resulting mixture was allowed to gradually warm to ambient temperature and then was refluxed for 15 minutes. The stirred mixture was cooled and a solution of 75 mmoles of isopropylmagnesium bromide (prepared from 2.1 g of magnesium turnings and 9.5 g of isopropyl bromide in 29 ml of anhydrous ether) was added dropwise at temperatures between 0° C. and +30° C. After refluxing for 4 hours, the reaction mixture was cooled to 0° C. and treated dropwise with 25 ml of water, thereby giving two phases. The ether phase was separated, dried over magnesium sulfate, concentrated, and distilled to give cyclohexylisopropylphenylphosphine: 31P-NMR δ=6.08 ppm; boiling point ("BP")=104°-105° C. at 0.05 torr, Chemical Ionization Mass Spec [M+H+ =235, yield=about 67%.

Workup

  1. additionAfter the addition
  2. temperatureto gradually warm to ambient temperature
  3. temperaturewas refluxed for 15 minutes
  4. temperatureThe stirred mixture was cooled
  5. temperatureAfter refluxing for 4 hours
  6. temperaturethe reaction mixture was cooled to 0° C.
  7. customgiving two phases
  8. customThe ether phase was separated
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. distillationdistilled

Sources & evidence

ORD record
ord-1bc44ea8ae3b489d992bbdb64b47c907
Source dataset
uspto-grants-1987_05
Patent number
US04668823

Reaction notes

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