Triethylamine → {2-Fluoro-3-[(trimethylsilyl)ethynyl]phenyl}methanol

HRID 1021260

Reaktionsgleichung

Reaktionsgleichung von HRID 1021260
[C:1]([Si:3]([CH3:6])([CH3:5])[CH3:4])#[CH:2].C(N(CC)CC)C.Br[C:15]1[C:16]([F:23])=[C:17]([CH2:21][OH:22])[CH:18]=[CH:19][CH:20]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I.CCOC(C)=O>[F:23][C:16]1[C:15]([C:2]#[C:1][Si:3]([CH3:6])([CH3:5])[CH3:4])=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:21][OH:22]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 269856463-Bromo-2-fluorobenzyl Alcohol

Produkt 1

HCID 86686224{2-Fluoro-3-[(trimethylsilyl)ethynyl]phenyl}methanol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Under argon atmosphere, ethynyl(trimethyl)silane (9.0 ml) was mixed with triethylamine (50 ml), and (3-bromo-2-fluorophenyl)methanol, bis(triphenylphosphine)palladium chloride (II) (1.54 g), and copper iodide (420 mg) were added thereto, followed by stirring at 90° C. overnight. The reaction mixture was cooled to room temperature, and EtOAc was added thereto, followed by filtering using Celite as a filtration adjuvant. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain {2-fluoro-3-[(trimethylsilyl)ethynyl]phenyl}methanol (4.88 g).

Aufarbeitung

  1. additionwere added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationby filtering
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-df3195c3b90844b58834d087b34f5f85
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716470B2

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