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

HRID 1358755

반응식

HRID 1358755 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-370048ee9b754305aaf87cc822d31ac9
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06596772B1

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