Triphenylphosphine → 1-(1-Ethynylhexyloxy)-2,3-difluorobenzene

HRID 1873308Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1873308
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[CH:10]#[C:11][CH:12](O)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.CC(OC)(C)C>[C:11]([CH:12]([O:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=1[F:1])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])#[CH:10]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 131661-Octyn-3-olHCID 808792,3-DifluorophenolHCID 5363146Diisopropyl azodicarboxylate

Produkt 1

HCID 592152391-(1-Ethynylhexyloxy)-2,3-difluorobenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

2.4 g (0.33 mol) of 2,3-difluorophenol are initially introduced in 1.2 l of THF together with 50.0 ml (0.34 mol) of 1-octyn-3-ol and 94.1 g (0.36 mol) of triphenylphosphine, and a solution of 76.1 ml (0.39 mol) of DIAD in 100 ml of THF is added dropwise. After 19 h at RT, the batch is diluted with MTBE and washed with water. The aqueous phase is extracted with MTBE, and the combined organic phases are washed with saturated sodium chloride solution. The solution is dried using sodium sulfate and evaporated to dryness. The residue is purified by column chromatography (SiO2, 1-chlorobutane), giving 1-(1-ethynylhexyloxy)-2,3-difluorobenzene as a colourless oil.

Aufarbeitung

  1. washwashed with water
  2. extractionThe aqueous phase is extracted with MTBE
  3. washthe combined organic phases are washed with saturated sodium chloride solution
  4. customThe solution is dried
  5. customevaporated to dryness
  6. customThe residue is purified by column chromatography (SiO2, 1-chlorobutane)

Quellen und Nachweise

ORD-Eintrag
ord-99a9c6d81ce54503a22202bff0fb1439
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08303844B2

Notizen zur Reaktion

Wird geladen…