Diiodomethane → 2-Iodo-5-(trifluoromethyl)benzonitrile

HRID 217490

Reaktionsgleichung

Reaktionsgleichung von HRID 217490
N[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5].N(OC(C)(C)C)=O.C(I)[I:22]>>[I:22][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5]

Komponenten

4

Edukt 3

HCID 6346DiiodomethaneHCID 10906Tert-Butyl nitriteHCID 126273614-Amino-3-cyanobenzotrifluoride

Produkt 1

HCID 533636442-Iodo-5-(trifluoromethyl)benzonitrile

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-Amino-5-(trifluoromethyl)benzonitrile (3.06 g, 16.45 mmol) was suspended in CH2I2 (36 mL) and t-butyl nitrite (3.9 mL, 32.9 mmol) was added dropwise by syringe. The reaction was heated slowly to 100° C. and was maintained at this temperature for 30 minutes. The reaction was then cooled to room temperature, diluted with hexanes (200 mL), loaded on a silica gel column, and purified with 100% hexanes to 15% EtOAc/hexanes. The resulting product, 2-iodo-5-(trifluoromethyl)benzonitrile was contaminated with minor impurities which were removed by silica gel chromatography with 25% CH2Cl2/hexanes. 2-Iodo-5-(trifluoromethyl)benzonitrile was obtained as a white solid. Rf=0.44 (15% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 8.10 (d, J=8.5 Hz, 1H), 7.85 (d, J=1.8 Hz, 1H), 7.52 (dd, J=8.5, 1.8 Hz, 1H).

Aufarbeitung

  1. temperaturewas maintained at this temperature for 30 minutes
  2. temperatureThe reaction was then cooled to room temperature
  3. custompurified with 100% hexanes to 15% EtOAc/hexanes
  4. customwere removed by silica gel chromatography with 25% CH2Cl2/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-608a3069a6674f66af4413952bb37d84
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193365B2

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