p-Bromochlorobenzene → (p-Chlorophenyl)(diethyl)phosphine

HRID 839575

Reaction equation

HRID 839575 reaction equation
[CH2:1]([P:3](Cl)[CH2:4][CH3:5])[CH3:2].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([Li])=[CH:10][CH:9]=1.ClC1C=CC(Br)=CC=1>CCOCC>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([P:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7806p-BromochlorobenzeneHCID 69639ChlorodiethylphosphineHCID 178506718HCID 178506718, compound

Product 1

HCID 20323571(p-Chlorophenyl)(diethyl)phosphine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 10 g. (0.08 mole) of diethylphosphinous chloride in 100 ml. of ether was added to a solution of p-chlorophenyllithium [prepared from 15.4 g. (0.08 mole) of p-chlorobromobenzene in 100 ml. of ether and 54 ml. of 1.5M n-butyllithium in hexane] under a nitrogen atmosphere. After 30 minutes, the reaction mixture was quenched with a few drops of ethyl acetate and the solvent was removed at reduced pressure. Distillation of the residual oil gave (p-chlorophenyl)(diethyl)phosphine, b.p. 86°-89° C. at 1.5 mm.

Workup

  1. customthe reaction mixture was quenched with a few drops of ethyl acetate
  2. customthe solvent was removed at reduced pressure
  3. distillationDistillation of the residual oil

Sources & evidence

ORD record
ord-3a32cbd09da144fd96f6f8bbc60fdf6d
Source dataset
uspto-grants-1978_06
Patent number
US04096250

Linked notes

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