Triethylamine → 1-[(Trimethylsilyl)ethynyl]-3-(trifluoromethyl)benzene

HRID 606792

Reaktionsgleichung

Reaktionsgleichung von HRID 606792
C(N(CC)CC)C.Br[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1.[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21]>C(OCC)(=O)C.[Cu]I.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:19][Si:20]([CH3:22])([CH3:21])[C:23]#[C:24][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 66111Trimethylsilylacetylene

Produkt 1

HCID 42818851-[(Trimethylsilyl)ethynyl]-3-(trifluoromethyl)benzeneAusbeute 102,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178419050HCID 178419050, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Add copper (I) iodide (48.2 mg, 0.25 mmol), bis(triphenylphosphine)palladium (II) dichloride (155.8 m g, 0.22 mmol) and triethylamine (2.51 mL, 17.8 mmol), to a solution of 1-bromo-3-trifluoromethylbenzene (0.62 mL, 4.44 mmol) and trimethylsilylacetylene (0.81 mL, 5.78 mmol), in ethyl acetate (4 mL). Stir at 50° C. for 18h. Cool the reaction mixture to room temperature, concentrate and purify the residue by silica gel chromatography, eluting with hexanes, to give the title compound (1.1 g, 100%).

Aufarbeitung

  1. temperatureCool the reaction mixture to room temperature
  2. concentrationconcentrate
  3. custompurify the residue by silica gel chromatography
  4. washeluting with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f63577125a7149d4866ada36ec1221d8
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915424B2

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