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

HRID 58197
ノート
印刷プレビュー

反応式

HRID 58197 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
150 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-1527a245572a4841aaa0af8fc180256a
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09434697B2

反応ノート

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