Dimethylformamide → Methyl 2',4'-dichloro-6-hydroxy-(1,1'-biphenyl)-carboxylate

HRID 133706Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 133706
O[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1I.CN(C=[O:17])C.[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1B(O)O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[C:4]1[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=[CH:2][C:3]=1[OH:17]

Komponenten

7

Edukt 3

HCID 6228DimethylformamideHCID 2734659(2,4-Dichlorophenyl)boronic acid2×HCID 11346465Methyl 4-hydroxy-3-iodobenzoate

Produkt 1

HCID 69309329Methyl 2',4'-dichloro-6-hydroxy-(1,1'-biphenyl)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 80271Tri-o-tolylphosphineKatalysator2×HCID 167845palladium(II) acetateKatalysator2×HCID 8471TriethylamineLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

5.6 g of methyl 4-hydroxy-3-iodobenzoate are introduced under argon into 50 ml of anhydrous DMF and then 4.2 g of 2,4-dichlorophenylboronic acid and 5.54 ml of triethylamine and then 240 mg of tri-orthotolylphosphine are added and the mixture is left under argon for 1 hour. 180 mg of palladium acetate are added and then the mixture is heated at 100° C. for 4 hours. 2 g of 2,4-dichlorophenylboronic acid, 5.54 ml of triethylamine, 120 mg of tri-orthotolylphoshine and 180 mg of palladium acetate are added and then the mixture is heated at 100° C. for 8 hours. It is concentrated under vacuum and the residue is taken up in AcOEt and then washed with 10% NH4OH solution. Extraction is carried out with AcOEt and the extract is washed with water and then with saturated NaCl solution. The residue is dried and then chromatographed on silica, eluting with a cyclohexane/AcOEt mixture (82/18; v/v), to give 3.4 g of the expected compound.

Aufarbeitung

  1. temperaturethe mixture is heated at 100° C. for 8 hours
  2. concentrationIt is concentrated under vacuum
  3. washwashed with 10% NH4OH solution
  4. extractionExtraction
  5. washthe extract is washed with water
  6. customThe residue is dried
  7. customchromatographed on silica
  8. washeluting with a cyclohexane/AcOEt mixture (82/18; v/v)

Quellen und Nachweise

ORD-Eintrag
ord-439f04e51ddc47fab0cdd8cdd0c18163
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390924B2

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