Triethyl phosphite → Diethyl (2,4-dimethylphenyl)phosphonate

HRID 217262

Reaktionsgleichung

Reaktionsgleichung von HRID 217262
I[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH3:9].[P:10]([O:17]CC)([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:12]([O:11][P:10]([C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH3:9])(=[O:17])[O:14][CH2:15][CH3:16])[CH3:13]

Komponenten

5

Edukt 2

HCID 31215Triethyl phosphiteHCID 778854-Iodo-m-xylene

Produkt 1

HCID 13836144Diethyl (2,4-dimethylphenyl)phosphonateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

4-Iodo-m-xylene (4.31 mmol), triethyl phosphite (6.03 mmol) and palladium acetate (0.43 mmol) were mixed together in acetonitrile (10 ml), in a microwave tube. The vessel was sealed and placed in a microwave to react at 160° C., for 45 minutes. After cooling to room temperature, acetonitrile was removed. The crude material was purified by silica gel chromatography (eluent: stepwise gradient of ethyl acetate (0-30%) in petroleum ether) to yield Intermediate I.1 as an oil (84%). Intermediate 1.1 was characterized by the following spectroscopic data: 1H NMR (CDCl3, 400 MHz) δ (ppm) 1.32 (t, J=8.0 Hz, 6H), 2.35 (s, 3H), 2.53 (s, 3H), 4.07-4.14 (m, 4H), 7.07-7.08 (m, 2H), 7.77-7.83 (m, 1H); 31P NMR (CDCl3, 162 MHz) δ (ppm) 20.15 (s, 1P); and MS (ESI, EI+) m/z=243 (MH+).

Aufarbeitung

  1. customThe vessel was sealed
  2. customto react at 160° C., for 45 minutes
  3. customacetonitrile was removed
  4. customThe crude material was purified by silica gel chromatography (eluent

Quellen und Nachweise

ORD-Eintrag
ord-8c51cdd718db47179a141401467a3d1f
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193372B2

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