Sodium hydride → 2-Hydroxy-5-(2-nitro-4-trifluoromethanesulfonyl-phenoxy)-terephthalic acid diethyl ester

HRID 1358755

Reaktionsgleichung

Reaktionsgleichung von HRID 1358755
[OH:1][C:2]1[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]([OH:18])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[H-].[Na+].[N+:21]([C:24]1[CH:29]=[C:28]([S:30]([C:33]([F:36])([F:35])[F:34])(=[O:32])=[O:31])[CH:27]=[CH:26][C:25]=1Cl)([O-:23])=[O:22]>C1COCC1>[CH2:16]([O:15][C:13](=[O:14])[C:11]1[CH:12]=[C:2]([O:1][C:25]2[CH:26]=[CH:27][C:28]([S:30]([C:33]([F:35])([F:36])[F:34])(=[O:32])=[O:31])=[CH:29][C:24]=2[N+:21]([O-:23])=[O:22])[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:9][C:10]=1[OH:18])[CH3:17]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 79980Diethyl 2,5-dihydroxyterephthalateHCID 15479561-chloro-2-nitro-4-[(trifluoromethyl)sulfonyl]benzene

Produkt 1

HCID 99578742-Hydroxy-5-(2-nitro-4-trifluoromethanesulfonyl-phenoxy)-terephthalic acid diethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of diethyl 2,5-dihydroxyterephthalate (100 mg, 0.393 mmol) in THF was added sodium hydride (32 mg of 60% dispersion in mineral oil) followed by 2-nitro-4-(trifluoromethylsulfonyl)chlorobenzene (228 mg, 0.787 mmol). The mixture was stirred at room temperature for overnight. The reaction was extracted with ethyl acetate, the organic layer was washed with water and brine, dried, concentrated and purified to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 10.77 (br s, 1H, OH), 8.78 (d, J=2.3 Hz, 1H), 8.22 (dd, J=2.3 & 9.0 Hz, 1H), 7.82(s, 1H), 7.56 (s, 1H), 7.19 (d, J=9.0 Hz, 1H), 4.32 (q, J=7.2 Hz, 2H, OCH2CH3), 4.09 (q, J=7.2 Hz, 2H, OCH2CH3), 1.3 (t, J=7.2 Hz, 3H, OCH2CH3), 0.92 (t, J=7.2 Hz, 3H, OCH2CH3).

Aufarbeitung

  1. extractionThe reaction was extracted with ethyl acetate
  2. washthe organic layer was washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-370048ee9b754305aaf87cc822d31ac9
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06596772B1

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