Ammonium Chloride → ({4-[(3-Fluorophenyl)methoxy]phenyl}ethynyl)(trimethyl)silane

HRID 2184352Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2184352
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10](I)=[CH:9][CH:8]=1.[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19].[Cl-].[NH4+]>C1COCC1.C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:22]#[C:21][Si:18]([CH3:20])([CH3:19])[CH3:17])=[CH:9][CH:8]=1

Komponenten

7

Edukt 3

HCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 224766211-Fluoro-3-[(4-iodophenoxy)methyl]benzene

Produkt 1

HCID 22476627({4-[(3-Fluorophenyl)methoxy]phenyl}ethynyl)(trimethyl)silane

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A well stirred suspension of 4.0 g (12.2 mmol) of 1-(3-fluorobenzyloxy)-4-iodo-benzene, 0.23 g (1.22 mmol) of cuprous iodide and 0.856 mg (1.22 mmol) of dichloro bis(triphenylphosphine) palladium(II) in a mixture of 20 ml THF and 10 ml triethylamine is treated dropwise with 1.44 g (14.6 mmol) of trimethylsilyl acetylene. The reaction is exothermic. The mixture is stirred overnight at RT, treated with saturated aqueous ammonium chloride and extracted three times with ethyl acetate. The organic phase is dried, concentrated and subjected to flash-chromatography (silica gel, cyclohexane) to yield 3.48 g (95%) of a slightly orange oil. NMR (CDCl3; 300 MHz): 0.24 ppm (s, 9H); 5.06 ppm (s, 2H); 6.85-7.45 ppm (m, 8H).

Aufarbeitung

  1. stirringThe mixture is stirred overnight at RT
  2. extractionextracted three times with ethyl acetate
  3. customThe organic phase is dried
  4. concentrationconcentrated
  5. customto yield 3.48 g (95%) of a slightly orange oil

Quellen und Nachweise

ORD-Eintrag
ord-4e7f55ff111443c98ea684cd3c74b685
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900354B2

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