Phenyl phosphorus dichloride → (2-Methylpropyl)(diphenyl)phosphane
Reaction equation
[CH2:1]([Mg]I)[CH:2]([CH3:4])[CH3:3].[C:7]1([P:13](Cl)Cl)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:16]1([Mg]Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCOCC>[CH2:1]([P:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH:2]([CH3:4])[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -25 °C
Procedure
265 ml of a 1.8 Molar titrated solution of 477 mmoles of isobutylmagnesium iodide in ether was added dropwise to a stirred solution of 85.35 g (476.8 mmoles) of phenyldichlorophosphine in 750 ml of anhydrous ether, maintained at -25° C. under an inert atmosphere. After stirring for 15 minutes at a temperature of -25° C., the reaction mixture was allowed to gradually warm to a temperature of 0° C. 308 ml of a 2.01 Molar solution of 620 mmoles of phenylmagnesium bromide in ether was added dropwise at a temperature of between 0° C. and +10° C., then the solution was warmed to reflux for one-half hour. The mixture was then hydrolyzed. Distillation yielded an impure isobutyldiphenylphosphine. 31P-NMR δ=-20.66 ppm (relative intensity 999.96), δ=-5.88 ppm (relative intensity 26.64 probably triphenylphosphine), δ=-34.23 ppm (relative intensity 74.75, probably diisobutylphenylphosphine), and δ=-60.57 ppm (relative intensity 123.65, probably (phenyl)(i-butyl)PH), BP=97°-101° C. at 0.15 torr.
Workup
- temperatureto gradually warm to a temperature of 0° C
- temperaturethe solution was warmed
- temperatureto reflux for one-half hour
- distillationDistillation
Sources & evidence
- ORD record
- ord-1c4680505e8d40bc844a8760b8e1ff0a
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04668823
Reaction notes
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