Bromobenzene → Triphenylphosphine Oxide

HRID 1884168Notes

Reaction equation

HRID 1884168 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1([PH:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[C:2]1([P:14](=[O:21])([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 254003Diphenylphosphine oxide

Product 1

HCID 13097Triphenylphosphine Oxide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 20 mL of reactor equipped with magnetic stir bar was charged with 93 mg (0.10 mmol) of {[(t-Bu)2P(OH)]2PdCl}2, 0.314 g (2.0 mmol) of bromobenzene, 0.404 g (2.0 mmol) of di-phenylphosphine oxide and 0.276 g (2.0 mmol) of K2CO3 in 5.0 mL of 1,4-dioxane. The resulting mixture was refluxed for 8 h to afford tri-phenylphosphine oxide. 31P NMR (CDCl3, 121 MHz): δ30.3 ppm.

Workup

  1. customA 20 mL of reactor equipped with magnetic stir bar
  2. temperatureThe resulting mixture was refluxed for 8 h

Sources & evidence

ORD record
ord-1c26293082144d2e830ec5c084370f24
Source dataset
uspto-grants-2004_07
Patent number
US06762330B2

Reaction notes

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