Iodine → HCID 11175139, Verbindung

HRID 1064755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1064755
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=[O:16])[CH3:15])[CH:9]=2)=[CH:4][CH:3]=1.[I-:17].[K+].II>N.O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14](=[O:16])[CH3:15])[CH:9]=2)=[CH:6][C:7]=1[I:17]

Komponenten

6

Edukt 3

HCID 807Iodine2×HCID 4875Potassium Iodide2×HCID 112181061-(4'-Hydroxy-1,1'-biphenyl-3-yl)ethanone

Produkt 1

HCID 11175139HCID 11175139, VerbindungAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 222AmmoniaLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

The product from Example 136A (5.76 g, 27 mmol) was suspended in concentrated aqueous ammonia (400 mL) and treated with a solution of potassium iodide (23.3 g, 140 mmol) and iodine (7.24 g, 28.5 mmol) in water (100 mL). As the reaction did not go to completion, the mixture was treated with a second solution of potassium iodide (15.8 g, 95 mmol) and iodine (4.83 g, 19 mmol) in water (50 mL). After an hour the ammonia was removed under reduced pressure on a rotary evaporator. The mixture was extracted with EtOAc, and the combined organic phases were washed consecutively with pH 6 potassium phosphate buffer and brine, then dried (Na2SO4), concentrated, and chromatographed through silica with 1% acetic acid in a gradient of 0 to 5% EtOAc/CH2Cl2 to provide the title compound as a beige powder (21% yield). MS (ESI APCI negative ion detection) m/z 337 (M−H)−; 1HNMR (300 MHz, CDCl3) δ 2.65 (s, 3 H), 5.37 (bs, 1 H), 7.08 (d, 1 H), 7.48-7.55 (m, 2 H), 7.71 (ddd, 1 H), 7.88-7.93 (m, 2 H), 8.09 (dd, 1 H).

Aufarbeitung

  1. customAfter an hour the ammonia was removed under reduced pressure on a rotary evaporator
  2. extractionThe mixture was extracted with EtOAc
  3. washthe combined organic phases were washed consecutively with pH 6 potassium phosphate buffer and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customchromatographed through silica with 1% acetic acid in a gradient of 0 to 5% EtOAc/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-e1525197e9e24935bf92fb7d452f01db
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06969730B2

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