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

HRID 13635

반응식

HRID 13635 반응식
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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e8606940710b406b8029a0d140bc9a4d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728137B2

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