Methyltriphenylphosphonium iodide → 1,2-Bis(difluoromethoxy)-4-vinylbenzene

HRID 1992347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1992347
[CH3:1]C(C)([O-])C.[K+].[I-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[F:28][CH:29]([F:43])[O:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=1[O:39][CH:40]([F:42])[F:41])[CH:34]=O>C1COCC1>[F:41][CH:40]([F:42])[O:39][C:38]1[CH:37]=[CH:36][C:33]([CH:34]=[CH2:1])=[CH:32][C:31]=1[O:30][CH:29]([F:43])[F:28]

Komponenten

5

Edukt 3

HCID 638159Methyltriphenylphosphonium iodideHCID 145092693,4-Bis(difluoromethoxy)benzaldehydeHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 685199461,2-Bis(difluoromethoxy)-4-vinylbenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Potassium tert-butoxide (6.7 g, 0.0683 mol) was taken in dry THF (25 mL) and stirred at 0° C. under a nitrogen atmosphere for 15 min. Methyl triphenylphosphonium iodide (27.6 g, 0.0683 mol; see step (ii) above) was then added, followed by 3,4-bis(difluoromethoxy)benzaldehyde (8 g, 0.034 mol; see step (i) above). The reaction mixture was then stirred for 1 h at RT, before being quenched with water. The organic solvents were evaporated under reduced pressure and the aqueous layer extracted with dichloromethane. Evaporation of the solvents followed, by chromatography of the residue over silica gel (using petroleum ether in ethyl acetate as eluent) afforded the sub-title compound as a pale yellow liquid. Yield: 6.5 g

Aufarbeitung

  1. stirringThe reaction mixture was then stirred for 1 h at RT
  2. custombefore being quenched with water
  3. customThe organic solvents were evaporated under reduced pressure
  4. extractionthe aqueous layer extracted with dichloromethane
  5. customEvaporation of the solvents

Quellen und Nachweise

ORD-Eintrag
ord-5659e3aad312417791223a22e8bd8b96
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07648985B2

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