Diiodomethane → 3-Iodo-5-(trifluoromethyl)benzyl alcohol

HRID 17057

Reaktionsgleichung

Reaktionsgleichung von HRID 17057
N[C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.N(OC(C)(C)C)=O.C(I)[I:22]>>[I:22][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Komponenten

4

Edukt 3

HCID 6346DiiodomethaneHCID 10906Tert-Butyl nitriteHCID 53414333(3-Amino-5-(trifluoromethyl)phenyl)methanol

Produkt 1

HCID 192615723-Iodo-5-(trifluoromethyl)benzyl alcohol

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

[3-amino-5-(trifluoromethyl)phenyl]methanol (500 mg, 5.2 mmol) was suspended in CH2I2 (5 mL) and t-butyl nitrite (622 μL, 5.2 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 (50 mL), loaded on a silica gel column, and purified with 100% hexanes to 25% EtOAc/hexanes to afford [3-iodo-5-(trifluoromethyl)phenyl]methanol. Rf=0.19 (15% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 7.91 (s, 1H), 7.87 (s, 1H), 7.59 (s, 1H), 4.73 (d, J=4.9 Hz, 2H), 1.86 (t, J=5.6 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 25% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-bcdbf29868c8476a87c9bbdc191742e7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737295B2

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