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Sulfuric Acid → 1-Fluoro-4-(1-methoxyethyl)-2-nitrobenzene

HRID 58197
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HRID 58197 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].S(=O)(=O)(O)O.[CH3:19]COC(C)=O.O>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:10][CH3:19])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]
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참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 179959151-(4-Fluoro-3-nitrophenyl)ethanolHCID 22728543Water ethylacetate

생성물 1

HCID 179959131-Fluoro-4-(1-methoxyethyl)-2-nitrobenzene수율 71%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
150 °C

실험 절차

1-(4-fluoro-3-nitrophenyl)ethanol (870 g, 4.7 mmol) was dissolved in MeOH (10 ml) and concentrated sulfuric acid (2.5 ml, 47 mmol) was added carefully. The reaction mixture was heated at 150° C. using microwave (Biotage Initiator) for 5 minutes. After cooling to room temperature, the reaction mixture was poured into EtOAc/water. The organic layer was washed with brine, dried over MgSO4 and evaporated. The resulting material was purified by flash chromatography on silica eluting with 0% to 50% EtOAc/Hexane to afford the title compound (664 mg, yield: 71%). 1H-NMR (400 MHz, CDCl3) δ 1.45 (d, 3H) 3.27 (s, 3H) 4.36 (q, 1H) 7.28-7.32 (m, 1H) 7.56-7.63 (m, 1H) 7.98-8.04 (m, 1H)

후처리

  1. customfor 5 minutes
  2. temperatureAfter cooling to room temperature
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe resulting material was purified by flash chromatography on silica eluting with 0% to 50% EtOAc/Hexane

출처 및 근거

ORD 기록
ord-1527a245572a4841aaa0af8fc180256a
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09434697B2

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