Ethyl Acetate → Methyl 5-fluoro-2-(2-nitrophenoxy)benzoate

HRID 718037

反応式

HRID 718037 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].F[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-:22])=[O:21])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 2783186Methyl 5-fluoro-2-hydroxybenzoate

生成物 1

HCID 59783776Methyl 5-fluoro-2-(2-nitrophenoxy)benzoate収率 84.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

Methyl 5-fluoro-2-hydroxybenzoate (2.65 g, 15.6 mmo.) and 1-fluoro-2-nitrobenzene (2.02 g, 14.2 mmol) were dissolved in acetonitrile (30 mL) and cesium carbonate (6.10 g, 18.7 mmol) was added. The reaction mixture was stirred at 80° C. for 60 hours. The mixture was cooled down to room temperature and poured into ethyl acetate. This organic mixture was washed with water and brine, dried over sodium sulfate, filtered and evaporated. The crude was purified by flash chromatography with 10-20% ethyl acetate in hexanes and triturated in ethanol to afford the title compound 18 (3.49 g, 84%) as white solid. LRMS (ESI): (calc) 291.05. (found) 292.2 (MS)+.

後処理

  1. temperatureThe mixture was cooled down to room temperature
  2. washThis organic mixture was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude was purified by flash chromatography with 10-20% ethyl acetate in hexanes
  7. customtriturated in ethanol

出典と根拠

ORDレコード
ord-2db8f05811d54b7591401200770970a1
出典データセット
uspto-grants-2015_11
特許番号
US09193749B2

関連ノート

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