Trimethylsilylacetylene → 2-Bromo-4-(trifluoromethyl)-6-[2-(trimethylsilyl)ethynyl]benzenamine

HRID 855281Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 855281
[Br:1][C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5](I)[C:3]=1[NH2:4].[C:14]([Si:16]([CH3:19])([CH3:18])[CH3:17])#[CH:15]>C(N(CC)CC)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>[Br:1][C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5]([C:15]#[C:14][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:3]=1[NH2:4]

Komponenten

6

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 269862642-Bromo-6-iodo-4-(trifluoromethyl)aniline

Produkt 1

HCID 693432912-Bromo-4-(trifluoromethyl)-6-[2-(trimethylsilyl)ethynyl]benzenamineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

To a solution of 7.54 g of 2-bromo-6-iodo-4-(trifluoromethyl)-aniline (21 mmol) in 70 ml triethylamine were added 723 mg of Pd(PPh3)2Cl2 (1 mmol), 196 mg of CuI (1 mmol) and 3.14 ml of ethinyltrimethylsilane (23 mmol). The reaction mixture was stirred for 3 h at rt before the triethylamine was removed under reduced pressure. Then DCM was added and the resulting suspension was filtered. The filtrate was then concentrated and the residue purified by chromatography (silica gel; c-hexane/EtOAc 19:1) to yield 6.51 g (94%) of 2-bromo-4-trifluoromethyl-6-trimethylsilanylethynyl-phenylamine as a dark brown liquid. 1H NMR (CDCl3, 300 MHz): δ 0.28 (s, 9H), 4.99 (br s, 2H), 7.51 (s, 1H), 7.61 (s, 1H).

Aufarbeitung

  1. customwas removed under reduced pressure
  2. additionThen DCM was added
  3. filtrationthe resulting suspension was filtered
  4. concentrationThe filtrate was then concentrated
  5. customthe residue purified by chromatography (silica gel; c-hexane/EtOAc 19:1)

Quellen und Nachweise

ORD-Eintrag
ord-d08cc1fb0b3b41309198afba0b3baa6c
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259183B2

Notizen zur Reaktion

Wird geladen…