Triethylamine → HCID 19821081, Verbindung

HRID 1030866

Reaktionsgleichung

Reaktionsgleichung von HRID 1030866
[F:1][C:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8](Br)[CH:7]=1)([F:4])[F:3].C(N(CC)CC)C.[NH2:20][C:21]1[CH:22]=[C:23]([C:27]#[CH:28])[CH:24]=[CH:25][CH:26]=1>CCOCC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:1][C:2]([F:4])([F:3])[O:5][C:6]1[CH:7]=[C:8]([C:28]#[C:27][C:23]2[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=2)[NH2:20])[CH:9]=[CH:10][CH:11]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 104682Benzenamine, 3-ethynyl-HCID 5199641-Bromo-3-(trifluoromethoxy)benzene

Produkt 1

HCID 19821081HCID 19821081, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11776TriphenylphosphineKatalysatorHCID 10122028Bis(triphenylphosphine)palladiumKatalysatorHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A multinecked flask as described in Example 1 was charged with 5.0 g (0.021 mol) of m-bromophenyl trifluoromethyl ether, 50 ml of dried, degassed triethylamine, 2.43 g (0.212 mol) of 3-aminophenylacetylene, 0.048 g (0.68 mmol) of bis(triphenylphosphine) palladium II chloride, 0.148 g (0.564 mmol) of triphenylphosphine, and 0.03 g (0.157 mmol) of cuprous iodide. The reaction mixture was heated at 65° C. for 20 hours at which point gas chromotography showed the reaction to be complete. The product mixture was cooled to room temperature and diluted with 75 ml of ether. Filtration of the insoluble triethylamine hydrobromide salt by-product followed by concentration of the filtrate gave the crude product as a viscous orange-colored liquid. Short path distillation of the crude product under reduced pressure gave 5.1 g (0.018 mol, 86% yield) of the purified product as a colorless liquid.

Aufarbeitung

  1. customA multinecked flask as described in Example 1
  2. customof dried
  3. customthe reaction
  4. temperatureThe product mixture was cooled to room temperature
  5. filtrationFiltration of the insoluble triethylamine hydrobromide salt by-product
  6. customgave the crude product as a viscous orange-colored liquid
  7. distillationShort path distillation of the crude product under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-060fe6916ebc47eaa012245b39deec3d
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05107026

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