Triethylamine → 3-[[3-(Trifluoromethyl)phenyl]ethynyl]aniline

HRID 1030864

Reaktionsgleichung

Reaktionsgleichung von HRID 1030864
Br[C:2]1[CH:3]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[NH2:19][C:20]1[CH:21]=[C:22]([C:26]#[CH:27])[CH:23]=[CH:24][CH:25]=1>[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.CCOCC>[F:9][C:8]([F:11])([F:10])[C:4]1[CH:3]=[C:2]([C:27]#[C:26][C:22]2[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=2)[NH2:19])[CH:7]=[CH:6][CH:5]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 104682Benzenamine, 3-ethynyl-

Produkt 1

HCID 198838763-[[3-(Trifluoromethyl)phenyl]ethynyl]anilineAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A multinecked round bottom flask fitted with a mechanical stirrer, reflux condenser, and thermometer was flushed and maintained under positive pressure of nitrogen. The flask was charged with 100.0 g (0.44 mol) of 3-bromobenzotrifluoride, 300 ml of dried, degassed triethylamine, 51.5 g (0.44 mol) of 3-aminophenylacetylene, 0.35 g (0.499 mmol) of bis(triphenylphosphine) palladium II chloride, 1.6 g (6.09 mmol) of (triphenylphosphine), and 0.1 g (0.52 mmol) of cuprous iodide. The reaction mixture was heated at 65° C. for 20 hours at which point gas chromatography showed the reaction to be complete. The product mixture was cooled to room temperature followed by the addition of 200 ml of ether. Removal of the triethylamine hydrobromide salt by-product by suction filtration followed by concentration of the filtrate under reduced pressure gave the crude product as a light off-white solid. Short path distillation of the crude product under reduced pressure gave 81.0 g (0.31 mol, 71% yield) of the product as a colorless liquid which crystallized on standing.

Aufarbeitung

  1. customA multinecked round bottom flask fitted with a mechanical stirrer
  2. temperaturereflux condenser
  3. customthermometer was flushed
  4. temperaturemaintained under positive pressure of nitrogen
  5. customof dried
  6. customthe reaction
  7. temperatureThe product mixture was cooled to room temperature
  8. customRemoval of the triethylamine hydrobromide salt by-product
  9. filtrationby suction filtration
  10. customgave the crude product as a light off-white solid
  11. distillationShort path distillation of the crude product under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a015b5de45ec4a52b31986bb48d5b00d
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05107026

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