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Dimethylformamide → Methyl 4-(trifluoromethyl)-1-benzothiophene-2-carboxylate

HRID 2271305
ノート
印刷プレビュー

反応式

HRID 2271305 の反応式
F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[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:6]1[C:3]2[CH:4]=[C:15]([C:14]([O:18][CH3:19])=[O:17])[S:16][C:2]=2[CH:9]=[CH:8][CH:7]=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 5219332-Fluoro-6-(trifluoromethyl)benzaldehyde

生成物 1

HCID 18526201Methyl 4-(trifluoromethyl)-1-benzothiophene-2-carboxylate収率 35.4%

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

反応条件

温度
130 °C

実験手順

A mixture of 1.00 g of 2-fluoro-6-(trifluoromethyl)benzaldehyde, 633 mg of methyl thioglycolate, 1.21 g of potassium carbonate and 15 ml of DMF was stirred at 130° C. for 2 hours. The reaction mixture was cooled to room temperature. To the reaction mixture was added water, and then 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 to obtain 480 mg of methyl 4-(trifluoromethyl)benzo[b]thiophene-2-carboxylate (the present compound 3).

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

出典と根拠

ORDレコード
ord-1d6e21acf49c416984f75fc425db3b8a
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09119396B2

反応ノート

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