1-Butyne → 2-But-1-ynyl-5-fluoro-phenylamine

HRID 1640247

Reaktionsgleichung

Reaktionsgleichung von HRID 1640247
[CH2:1]1[CH2:5]O[CH2:3][CH2:2]1.[F:6][C:7]1[CH:8]=[CH:9][C:10](I)=[C:11]([CH:13]=1)[NH2:12].C(N(CC)CC)C.C#CCC>C(OCC)C.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>[C:5]([C:10]1[CH:9]=[CH:8][C:7]([F:6])=[CH:13][C:11]=1[NH2:12])#[C:1][CH2:2][CH3:3]

Komponenten

8

Edukt 4

HCID 78461-ButyneHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 27745125-Fluoro-2-iodoaniline

Produkt 1

HCID 581174762-But-1-ynyl-5-fluoro-phenylamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

160 mL of THF were placed in the flask and degassed with argon. Then 10 g (45 mmol) 5-fluoro-2-iodo-aniline, 1.5 g (2.1 mmol) PdCl2(PPh3)2 and 0.40 g (2.1 mmol) copper iodide were added and the flask was rinsed with argon. Then 18 mL (0.13 mol) triethylamine were added and 3.0 g (55 mmol) 1-butyne (in gaseous form) were passed through the solution. The reaction mixture was stirred for 3 h at RT, then diluted with diethyl ether, filtered through kieselguhr and evaporated down.

Aufarbeitung

  1. customdegassed with argon
  2. washthe flask was rinsed with argon
  3. filtrationfiltered through kieselguhr
  4. customevaporated down

Quellen und Nachweise

ORD-Eintrag
ord-db4a19ae8e89483987734dd1bd3132c5
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110575B2

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