Hydrochloric Acid → 4'-Isopropoxy-2'-methylbiphenyl-2-ol

HRID 46278

Reaktionsgleichung

Reaktionsgleichung von HRID 46278
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH:9]([O:12][C:13]1[CH:18]=[CH:17][C:16](B2OC(C)(C)C(C)(C)O2)=[C:15]([CH3:28])[CH:14]=1)([CH3:11])[CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>COCCOC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH:9]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[C:3]([OH:8])=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:15]([CH3:28])[CH:14]=1)([CH3:10])[CH3:11]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 107842-IodophenolHCID 10796Cesium carbonateHCID 594365172-(4-Isopropoxy-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 594365614'-Isopropoxy-2'-methylbiphenyl-2-olAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

2-Iodophenol (1.54 g, 7.00 mmol) was combined with 2-(4-isopropoxy-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Preparation 38, 2.00 g, 7.24 mmol), cesium carbonate (4.56 g, 13.99 mmol) and palladium tetrakis(triphenylphosphine) (0.24 g, 0.21 mmol) in 1,2-dimethoxyethane (40 mL). The reaction mixture was heated to reflux for 18 hours. The reaction mixture was cooled to room temperature and then acidified with a 1 N aqueous HCl solution. The organics were extracted 3 times with diethylether. The organic layers were combined, washed with brine, dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography using as eluant a mixture heptane/ethyl acetate to afford 543 mg (31% yield) of 4′-isopropoxy-2′-methylbiphenyl-2-ol as a pale yellow oil. MS m/z 243 [MH]+

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 hours
  3. extractionThe organics were extracted 3 times with diethylether
  4. washwashed with brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-79aca5150d334676b144873eb28a3a22
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541588B2

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