Toluene → 2-Phenylfuran

HRID 659105

Reaktionsgleichung

Reaktionsgleichung von HRID 659105
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.Br[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1(C)C=CC=CC=1>CCO>[C:10]1([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 7961BromobenzeneHCID 10796Cesium carbonateHCID 2734357Furan-2-boronic acid

Produkt 1

HCID 5193632-Phenylfuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

Furan-2-boronic acid (22) (3.6 g, 32.14 mmol) was coupled to bromobenzene (21) (4.2 g, 26.79 mmol) using Method E, except that Cs2CO3 (17.47 g, 53.58 mmol), Pd(PPha)4 (6.20 g, 0.54 mmol), toluene (25 mL) and EtOH (25 mL) were used and the reaction heated in a CEM Discover microwave at 140° C. (200 W, 200 psi). The crude product was purified by dry-flash chromatography eluting with EtOAc in heptane to yield the title compound. Yield: 2.94 g, 62%; LC tr 1.50 min; HPLC Purity: 84%

Aufarbeitung

  1. customThe crude product was purified by dry-flash chromatography
  2. washeluting with EtOAc in heptane

Quellen und Nachweise

ORD-Eintrag
ord-c5527ea8e52d4a509b9aae5f8e6b5360
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080567B2

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