Water → 4-Hydroxy-(1,1'-biphenyl)-3-carbaldehyde

HRID 1043694

Reaktionsgleichung

Reaktionsgleichung von HRID 1043694
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)Cl.[C:13]([O-:16])([O-])=O.[Na+].[Na+].[OH2:19]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:19][C:1]1[CH:6]=[CH:5][C:4]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:3][C:2]=1[CH:13]=[O:16]

Komponenten

7

Edukt 4

HCID 962WaterHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic Acid

Produkt 1

HCID 122646584-Hydroxy-(1,1'-biphenyl)-3-carbaldehydeAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 18180031Water 1,2-dimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

(Fahmy, A. M.; Revue Roumaine de Chimie 1985, V30(8), P749-52) Bromosalicaldehyde (S1, 525 mg, 2.6 mmol), phenylboronic acid (S2, 349 mg, 2.86 mmol), Pd(dppf)Cl2.CH2Cl2 (106 mg, 0.13 mmol) and Na2CO3 (413 mg, 3.9 mmol) were dissolved in degassed DME/H2O (3:1) and stirred at reflux (100° C.) for 5 h. After cooling, the mixture was poured into water and extracted with DCM (3×100 ml). The combined organic layers were dried over Na2SO4 and the residue purified by silica gel chromatography (Et2O, 100%) to afford the title compound (250 mg, 50%).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with DCM (3×100 ml)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customthe residue purified by silica gel chromatography (Et2O, 100%)

Quellen und Nachweise

ORD-Eintrag
ord-e81718c76b784abb83d3e438479e8b3f
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563557B2

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