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Dimethylformamide → 5-Trifluoromethyl-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 589279
ノート
印刷プレビュー

反応式

HRID 589279 の反応式
F[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH:4]=O.[C:14]([O:18][CH3:19])(=[O:17])[CH2:15][SH:16].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:11][C:10]([F:13])([F:12])[C:7]1[CH:8]=[CH:9][C:2]2[S:16][C:15]([C:14]([O:18][CH3:19])=[O:17])=[CH:4][C:3]=2[CH:6]=1
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

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 27349042-Fluoro-5-(trifluoromethyl)benzaldehyde

生成物 1

HCID 14779565-Trifluoromethyl-benzo[b]thiophene-2-carboxylic acid methyl ester収率 93%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

反応条件

温度
60 °C

実験手順

A mixture of 5.0 g of 2-fluoro-5-(trifluoromethyl)benzaldehyde, 3.3 g of methyl thioglycolate, 4.0 g of potassium carbonate and 50 ml of DMF was stirred at 60° C. for 2 hours, and then the reaction mixture was cooled to room temperature. To the reaction mixture was added water, and extracted with tert-butyl methyl ether 3 times. The combined organic layer was washed with water, followed by saturated aqueous sodium chloride solution. The mixture was dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was recrystallized from methanol to obtain 6.3 g of methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate.

後処理

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionextracted with tert-butyl methyl ether 3 times
  3. washThe combined organic layer was washed with water
  4. dry with materialThe mixture was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from methanol

出典と根拠

ORDレコード
ord-97ed15902577462c99ed5940edf75a7f
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09232792B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート