Dichloromethane → 1-(4'-Hydroxy-1,1'-biphenyl-3-yl)ethanone

HRID 1064754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1064754
I[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]([C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1)(=[O:11])[CH3:10].C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([C:9](=[O:11])[CH3:10])[CH:17]=2)=[CH:3][CH:4]=1

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 108944-IodophenolHCID 27343103-Acetylphenylboronic acid

Produkt 1

HCID 112181061-(4'-Hydroxy-1,1'-biphenyl-3-yl)ethanoneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

4-Iodophenol (5.39 g, 24.5 mmol) and 3-acetylphenylboronic acid (4.42 g, 26.95 mmol) were mixed in N,N-dimethylformamide (15 mL) and treated with 1.0 M aqueous Na2CO3 (75 mL) and palladium (II) acetate (110 mg, 0.49 mmol). The suspension was heated at 55° C. for one hour and then brought to room temperature. CH2Cl2 (100 mL) was added to the mixture which was then filtered. The aqueous layer of the filtrate was extracted with CH2Cl2 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 a 33 to 100% gradient of hexanes/CH2Cl2 followed by a gradient of 0 to 3% EtOAc/CH2Cl2. Impure fractions were combined, concentrated, and rechromatographed as before, twice, to provide the title compound as an oil which slowly crystallized to a white solid upon standing (˜95% yield). MS (ESI APCI negative ion detection) m/z 211 (M−H)−; 1HNMR (300 MHz, CDCl3) δ 2.65 (s, 3 H), 6.97 (d, 2 H), 7.47-7.53 (m, 3 H), 7.74 (ddd, 1 H), 7.88 (ddd, 1 H), 8.13 (dd, 1 H).

Aufarbeitung

  1. custombrought to room temperature
  2. filtrationwas then filtered
  3. extractionThe aqueous layer of the filtrate was extracted with CH2Cl2
  4. washthe combined organic phases were washed consecutively with pH 6 potassium phosphate buffer and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customchromatographed through silica with a 33 to 100% gradient of hexanes/CH2Cl2
  8. concentrationconcentrated
  9. customrechromatographed as before, twice,

Quellen und Nachweise

ORD-Eintrag
ord-d05721e7d0504321af4f001c89053d0a
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06969730B2

Notizen zur Reaktion

Wird geladen…