Tris(1,1-dimethylethyl)phosphine → Tris(6-(2-methoxyphenyl)-2-pyridyl)phosphine oxide

HRID 13635

Reaction equation

HRID 13635 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([P:8](=[O:23])([C:16]2[N:21]=[C:20](Br)[CH:19]=[CH:18][CH:17]=2)[C:9]2[N:14]=[C:13](Br)[CH:12]=[CH:11][CH:10]=2)[N:3]=1.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O.[F-].[K+].C(P([C:46]([CH3:49])([CH3:48])C)C(C)(C)C)(C)(C)C>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(OCC)(=O)C>[CH3:24][O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:2]1[N:3]=[C:4]([P:8](=[O:23])([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]([C:48]3[CH:46]=[CH:49][CH:28]=[CH:27][C:26]=3[O:25][CH3:24])[N:21]=2)[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[O:25][CH3:24])[N:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 522689Potassium FluorideHCID 27339582-Methoxyphenylboronic acidHCID 21708779Tris(2-bromo-6-pyridyl)phosphine oxide

Product 1

HCID 86608172Tris(6-(2-methoxyphenyl)-2-pyridyl)phosphine oxide

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

An efficiently stirred suspension of 38.8 g (75.0 mmol) of tris(2-bromo-6-pyridyl)phosphine oxide, 51.3 g (337.5 mmol) of 2-methoxybenzeneboronic acid and 43.1 g (742.5 mmol) of potassium fluoride in 750 ml of anhydrous THF was admixed with 593 mg (2.93 mmol) of tri-tert-butylphosphine and then with 505 mg (2.25 mmol) of palladium(II) acetate, and subsequently heated under reflux for 16 h. After cooling, the reaction mixture was admixed with 1500 ml of ethyl acetate and 1000 ml of water. The organic phase was removed, washed twice with 500 ml of water and once with 500 ml of sat. sodium chloride solution, and subsequently dried over magnesium sulfate. After the organic phase had been concentrated under reduced pressure (end pressure 1 mbar, temperature 90° C.), 44.3 g (98.5%) of a pale yellow highly viscous oil remained, which was reacted further without purification.

Workup

  1. temperatureunder reflux for 16 h
  2. temperatureAfter cooling
  3. customThe organic phase was removed
  4. washwashed twice with 500 ml of water and once with 500 ml of sat. sodium chloride solution
  5. dry with materialsubsequently dried over magnesium sulfate
  6. concentrationAfter the organic phase had been concentrated under reduced pressure (end pressure 1 mbar, temperature 90° C.), 44.3 g (98.5%) of a pale yellow highly viscous oil
  7. customwhich was reacted further without purification

Sources & evidence

ORD record
ord-e8606940710b406b8029a0d140bc9a4d
Source dataset
uspto-grants-2010_06
Patent number
US07728137B2

Linked notes

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