Water → 3-Iodo-3'-(trifluoromethyl)biphenyl-4-ol

HRID 1619622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619622
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[I:18]N1C(=O)CCC1=O.O>C(O)(=O)C>[I:18][C:11]1[CH:10]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:16])([F:17])[F:1])[CH:4]=2)[CH:14]=[CH:13][C:12]=1[OH:15]

Komponenten

5

Edukt 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 200995974-(3-Trifluoromethylphenyl)phenol

Produkt 1

HCID 580422843-Iodo-3'-(trifluoromethyl)biphenyl-4-olAusbeute 39,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 3′-(trifluoromethyl)biphenyl-4-ol (Preparation 1, 2.17 g, 9.11 mmol) in acetic acid (20 mL) at 0° C. was added N-iodosuccinimide (2.05 g, 9.11 mmol). The reaction was allowed to warm to room temperature and stirred for 48 hours before the addition of water (20 mL). The reaction mixture was extracted with dichloromethane (2×20 mL) and the combined extracts were washed with saturated aqueous sodium thiosulfate solution, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (2%-20% ethyl acetate in heptane gradient elution) to afford the title compound (1.30 g, 39%).

Aufarbeitung

  1. extractionThe reaction mixture was extracted with dichloromethane (2×20 mL)
  2. washthe combined extracts were washed with saturated aqueous sodium thiosulfate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (2%-20% ethyl acetate in heptane gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-e79e6675d1bb47ee9f6ca1128ea2c540
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772293B2

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