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Pyridine → 4-tert-Butyl-2-nitrophenyl trifluoromethanesulfonate

HRID 735790
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HRID 735790 반응식
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[C:16]([C:20]1[CH:25]=[CH:24][C:23](O)=[C:22]([N+:27]([O-:29])=[O:28])[CH:21]=1)([CH3:19])([CH3:18])[CH3:17].N1C=CC=CC=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:16]([C:20]1[CH:25]=[CH:24][C:23]([O:8][S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2])=[C:22]([N+:27]([O-:29])=[O:28])[CH:21]=1)([CH3:19])([CH3:17])[CH3:18]
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참가 물질

6

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HCID 1049PyridineHCID 18661Phenol, 4-(1,1-dimethylethyl)-2-nitro-HCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium Bicarbonate

생성물 1

HCID 231090154-tert-Butyl-2-nitrophenyl trifluoromethanesulfonate수율 87%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

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온도
0 °C

실험 절차

Triflic anhydride (4.14 mL, 24.6 mmol) was added dropwise to a solution of 4-tert-butyl-2-nitrophenol (4.00 g, 20.5 mmol) and pyridine (2.16 mL, 26.7 mmol) in methylene chloride (50 mL) at 0° C. The yellow solution was stirred 0.25 h at 0° C., poured onto saturated aqueous NaHCO3 and extracted with methylene chloride. The combined extracts were washed with saturated aqueous NaHCO3, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by filtration through a plug of silica-gel (methylene chloride) to provide trifluoro-methanesulfonic acid 4-tert-butyl-2-nitro-phenyl ester (5.82 g, 87%) as a pale yellow oil which was utilized without further purification.

후처리

  1. extractionextracted with methylene chloride
  2. washThe combined extracts were washed with saturated aqueous NaHCO3
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationThe residue was purified by filtration through a plug of silica-gel (methylene chloride)

출처 및 근거

ORD 기록
ord-92b71e5b944a48ada13a8cc0ebbbeb58
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07592332B2

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