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

HRID 1358755

反応式

HRID 1358755 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-370048ee9b754305aaf87cc822d31ac9
出典データセット
uspto-grants-2003_07
特許番号
US06596772B1

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