Iodoform → 4-Carboxy-2-iodobenzotrifluoride, 3-Iodo-alpha,alpha,alpha-trifluoro-p-toluic acid

HRID 423360

Reaktionsgleichung

Reaktionsgleichung von HRID 423360
N[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[C:5]([OH:7])=[O:6].[I:15]C(I)I.N(OCCCC)=O>C1COCC1>[I:15][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[C:5]([OH:7])=[O:6]

Komponenten

5

Edukt 3

HCID 6374IodoformHCID 10996Butyl nitriteHCID 6426513-Amino-4-(trifluoromethyl)benzoic acid2×

Produkt 1

HCID 593184244-Carboxy-2-iodobenzotrifluoride, 3-Iodo-alpha,alpha,alpha-trifluoro-p-toluic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-Amino-4-(trifluoromethyl)benzoic acid (commercially available) (6.5 g, 31.7 mmol) and triiodomethane (37.4 g, 95.1 mmol) were dissolved in THF (300 ml). The reaction mixture was heated to 80° C. and then butyl nitrite (5.56 ml, 47.6 mmol) was added slowly at this temperature. Heating was continued at this temperature for 4 hours and then the reaction was concentrated in vacuo to give the crude product. Purification by column chromatography (hexane to 30% EtOAc in hexane). This material was combined with another batch from a similar reaction performed on 2 g of 3-amino-4-(trifluoromethyl)benzoic acid. The combined material was purified by preparative HPLC to give the title compound (6.1 g). MS C8H4F3IO2 requires 316; found 315 (M−H+).

Aufarbeitung

  1. temperatureHeating
  2. concentrationthe reaction was concentrated in vacuo
  3. customto give the crude product
  4. customPurification by column chromatography (hexane to 30% EtOAc in hexane)
  5. customThis material was combined with another batch from a similar reaction
  6. customThe combined material was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-8c22aa50f5d6404d9219efda24c2f897
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101775B2

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