N-Iodosuccinimide → 3-Bromo-2-iodo-5-(trifluoromethyl)aniline

HRID 931001

Reaktionsgleichung

Reaktionsgleichung von HRID 931001
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5].[I:13]N1C(=O)CCC1=O>C(O)(=O)C.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([I:13])=[C:4]([CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1)[NH2:5]

Komponenten

5

Edukt 2

HCID 120273N-IodosuccinimideHCID 27358803-Bromo-5-(trifluoromethyl)aniline

Produkt 1

HCID 575461423-Bromo-2-iodo-5-(trifluoromethyl)anilineAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-bromo-5-(trifluoromethyl)aniline (5.00 g) in acetic acid (40 mL) was added N-iodosuccinimide (5.16 g) at 0° C., and the mixture was stirred overnight at room temperature under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate, washed with 10% aqueous sodium thiosulfate solution, saturated aqueous sodium bicarbonate solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (5.21 g). 1H NMR (300 MHz, CDCl3) δ 4.58 (2H, brs), 6.84 (1H, d, J=1.1 Hz), 7.23 (1H, d, J=1.1 Hz).

Aufarbeitung

  1. washwashed with 10% aqueous sodium thiosulfate solution, saturated aqueous sodium bicarbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4742f0dfcf32470bad86ff75ea01a13b
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296746B2

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