Hydrochloric Acid → 5-(2,4,5-Trifluorophenyl)-3-pentyn-1-ol

HRID 2050648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2050648
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[F:10].[CH2:11]([OH:16])[CH2:12][CH2:13][C:14]#[CH:15].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>C(N(CC)CC)C.[Pd].[Cu]I>[F:10][C:3]1[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=1[CH2:15][C:14]#[C:13][CH2:12][CH2:11][OH:16]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 675971-Bromo-2,4,5-trifluorobenzeneHCID 793464-Pentyn-1-olHCID 22619264Triphenyl phosphine chloride

Produkt 1

HCID 200587085-(2,4,5-Trifluorophenyl)-3-pentyn-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 1-bromo-2,4,5-trifluorobenzene (5.0 g, 23.7 mmol), 4-pentyn-1-ol (2.4 ml, 26 mmol), palladium bis(triphenylphosphine chloride (5 mg), copper (I) iodide (5 mg) in triethylamine (30 ml) was refluxed under argon for 10 hours. On cooling, the mixture was acidified with dilute hydrochloric acid and was extracted with ethyl ether. Evaporation of the extracts gave an oil, which was purified by chromatography on a silica column using 60% ethyl ether/hexane to give the title alcohol.

Aufarbeitung

  1. temperaturewas refluxed under argon for 10 hours
  2. temperatureOn cooling
  3. extractionwas extracted with ethyl ether
  4. customEvaporation of the extracts
  5. customgave an oil, which
  6. customwas purified by chromatography on a silica column

Quellen und Nachweise

ORD-Eintrag
ord-3176bd6e97ba40288a1792136a6e19ff
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05013850

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