Trimethylsilylacetylene → 3-Bromo-5-(trifluoromethyl)-2-[(trimethylsilyl)ethynyl]aniline

HRID 913897

Reaktionsgleichung

Reaktionsgleichung von HRID 913897
[Br:1][C:2]1[C:3](I)=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5].[CH3:14][Si:15]([C:18]#[CH:19])([CH3:17])[CH3:16]>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[C:3]([C:19]#[C:18][Si:15]([CH3:17])([CH3:16])[CH3:14])=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5]

Komponenten

6

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 575461423-Bromo-2-iodo-5-(trifluoromethyl)aniline

Produkt 1

HCID 575462013-Bromo-5-(trifluoromethyl)-2-[(trimethylsilyl)ethynyl]aniline

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-Bromo-2-iodo-5-(trifluoromethyl)aniline (18.7 g, 51.1 mmol) was dissolved in triethylamine (400 mL). To this was added dichlorobis(triphenylphosphine)palladium(II) (3.59 g, 5.11 mmol), copper(I) iodide (0.973 g, 5.11 mmol), and trimethylsilylacetylene (5.52 g, 56.2 mmol). The reaction was stirred for 2 h at ambient temperature, at 80° C. for 2 h, and then evaporated. The residue was purified by chromatography on silica gel with 5% ethyl acetate/hexanes to give 10.67 g (62.1%) as a brown liquid. 1H-NMR (CDCl3, 400 MHz) δ 7.13 (s, 1H), 6.82 (s, 1H), 4.52 (bs, 2H), 0.29 (s, 9H); LC/MS (HPLC method 4): tR=4.208 min, 336.05(MH)+.

Aufarbeitung

  1. customevaporated
  2. customThe residue was purified by chromatography on silica gel with 5% ethyl acetate/hexanes
  3. customto give 10.67 g (62.1%) as a brown liquid

Quellen und Nachweise

ORD-Eintrag
ord-007ea7fb7a5d426b94102d884d1b418c
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026257B2

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