Triethylamine → 4-(Biphenyl-2-yloxy)-3-cyano-benzenesulfonic acid pentafluorophenyl ester

HRID 1692251

반응식

HRID 1692251 반응식
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][C:9]=1[C:18]#[N:19].[F:26][C:27]1[C:32]([OH:33])=[C:31]([F:34])[C:30]([F:35])=[C:29]([F:36])[C:28]=1[F:37].CCN(CC)CC>ClCCl>[F:26][C:27]1[C:32]([O:33][S:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[C:9]([C:18]#[N:19])[CH:10]=2)(=[O:16])=[O:15])=[C:31]([F:34])[C:30]([F:35])=[C:29]([F:36])[C:28]=1[F:37]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 13041PentafluorophenolHCID 594365064-(Biphenyl-2-yloxy)-3-cyanobenzenesulfonyl chloride

생성물 1

HCID 594364764-(Biphenyl-2-yloxy)-3-cyano-benzenesulfonic acid pentafluorophenyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 4-(biphenyl-2-yloxy)-3-cyano-benzenesulfonyl chloride (Preparation 55, 500 mg, 1.35 mmol) in dichloromethane (5 ml) was added slowly to pentafluorophenol (249 mg, 1.35 mmol) and Et3N (137 mg, 1.35 mmol) in dichloromethane (5 ml) and stirring continued overnight at ambient temperature. The reaction was concentrated in vacuo and purified using silica gel column chromatography (dichloromethane/heptane 40/60, then 60/40, then 80/20, then dichloromethane) to furnish the title compound. LCMS Rt=1.92 minutes 1H NMR (400 MHz; CDCl3) δ (ppm): 6.69 (d, J=8.98 Hz, 1 H) 7.21-7.30 (m, 2 H) 7.31-7.38 (m, 2 H) 7.43-7.53 (m, 4 H) 7.53-7.58 (m, 1 H) 7.79 (dd, J=8.98, 2.34 Hz, 1 H) 8.06 (d, J=2.34 Hz, 1 H) 19F NMR (376 MHz, CDCl3) δ (ppm): 160.82 (t, J=19.50 Hz) −154.87 (t, J=21.80 Hz) −151.09 (d, J=17.21 Hz)

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified

출처 및 근거

ORD 기록
ord-1376d09a6eb94116b1eca581b1020bcb
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153814B2

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