Phenyl phosphorus dichloride → Isopropyldiphenylphosphine

HRID 979715

Reaction equation

HRID 979715 reaction equation
[CH:1]([Mg]Br)([CH3:3])[CH3:2].[C:6]1([P:12](Cl)Cl)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:15]1([Mg]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CCOCC>[CH:1]([P:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 12573Phenyl phosphorus dichlorideHCID 178418255HCID 178418255, compoundHCID 178418365HCID 178418365, compound

Product 1

HCID 80754IsopropyldiphenylphosphineYield 49%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-25 °C

Procedure

193 ml of a 2.6 Molar solution of 503 mmoles of isopropylmagnesium bromide in ether was added dropwise to a stirred solution of 89.96 g (502.6 mmoles) of phenyldichlorophosphine in 750 ml of anhydrous ether, maintained at -25° C. under an inert atmosphere. After the addition was complete, the mixture was stirred for 15 minutes at a temperature of -25° C. and then was allowed to gradually warm to +8° C. 325 ml of a 2.01 Molar solution of 653 mmoles of phenylmagnesium bromide in ether was then added dropwise at a temperature of between +8° C. to +32° C. The mixture was refluxed for one-half hour, and hydrolyzed. Distillation gave isopropyldiphenylphosphine. 31P-NMR(delta)=0.49 ppm (relative intensity 999.96), Yield=about 49%, BP=122°-124° C. at 0.3 torr.

Workup

  1. additionAfter the addition
  2. temperatureto gradually warm to +8° C
  3. temperatureThe mixture was refluxed for one-half hour
  4. distillationDistillation

Sources & evidence

ORD record
ord-6ec79bbd0ff34c71897b9005d6984e71
Source dataset
uspto-grants-1987_05
Patent number
US04668823

Linked notes

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