Cesium carbonate → Ethyl 2-methyl-4-(4-(methylsulfonyl)phenoxy)benzofuran-6-carboxylate

HRID 1177255Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177255
[OH:1][C:2]1[C:7]2[CH:8]=[C:9]([CH3:11])[O:10][C:6]=2[CH:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:3]=1.F[C:18]1[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:11][C:9]1[O:10][C:6]2[CH:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:3]=[C:2]([O:1][C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)[C:7]=2[CH:8]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 11514065Ethyl 4-hydroxy-2-methylbenzofuran-6-carboxylate

Produkt 1

HCID 59560179Ethyl 2-methyl-4-(4-(methylsulfonyl)phenoxy)benzofuran-6-carboxylateAusbeute 66,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

The mixture of ethyl 4-hydroxy-2-methylbenzofuran-6-carboxylate (4.5 g, 20.4 mmol), 1-fluoro-4-(methylsulfonyl)benzene (5.34 g, 30.7 mmol) and Cs2CO3 (9.99 g, 30.7 mmol) in DMF (10 mL) was heated in a microwave at 120° C. for 60 min. The sample was filtered and the filtrate was concentrated to give an oil residue. The oil was purified by HPLC to give the title compound (5.074 g, 66%) as an off-white solid. 1H NMR (300 MHz, CHLOROFORM-D) d ppm 1.39 (t, J=7.16 Hz, 3 H) 2.46 (s, 3 H) 3.06 (s, 3 H) 4.38 (q, J=7.16 Hz, 2 H) 6.21 (s, 1 H) 7.00-7.14 (m, 2 H) 7.62 (s, 1 H) 7.81-7.95 (m, 2 H) 8.01 (s, 1 H).

Aufarbeitung

  1. filtrationThe sample was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give an oil residue
  4. customThe oil was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-c1351deb94f144a78f8bc7f03abeeb55
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842713B2

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