Dimethyl Sulfoxide → 5-(4-Fluorophenoxy)thiophene-2-carbonitrile

HRID 78059

反応式

HRID 78059 の反応式
CS(C)=O.[N+]([C:8]1[S:12][C:11]([C:13]#[N:14])=[CH:10][CH:9]=1)([O-])=O.[F:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>O>[F:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:8]2[S:12][C:11]([C:13]#[N:14])=[CH:10][CH:9]=2)=[CH:18][CH:17]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 5192945-Nitrothiophene-2-carbonitrile

生成物 1

HCID 231305625-(4-Fluorophenoxy)thiophene-2-carbonitrile収率 85.9%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

To a dimethyl sulfoxide (100 mL) solution of 5-nitro-2-thiophene carbonitrile (5.00 g, 32.4 mmol) were added 4-fluorophenol (5.45 g, 48.6 mmol) and potassium carbonate (11.2 g, 81.0 mmol) under nitrogen atmosphere, which was stirred for 16 hours at 60° C. The reaction solution was cooled to room temperature and water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:10→1:5) to obtain the title compound (6.10 g, 85.9%).

後処理

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:10→1:5)

出典と根拠

ORDレコード
ord-e032a5b32a4a429b9fe270faaaf34eb1
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

関連ノート

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