Dimethylformamide → Methyl 6-(trifluoromethyl)-1-benzothiophene-2-carboxylate

HRID 589281ノート

反応式

HRID 589281 の反応式
F[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[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:8]1[CH:7]=[CH:6][C:3]2[CH:4]=[C:15]([C:14]([O:18][CH3:19])=[O:17])[S:16][C:2]=2[CH:9]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 5229292-Fluoro-4-(trifluoromethyl)benzaldehyde

生成物 1

HCID 18526202Methyl 6-(trifluoromethyl)-1-benzothiophene-2-carboxylate収率 56.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

A mixture of 1.11 g of 2-fluoro-4-(trifluoromethyl)benzaldehyde, 739 mg of methyl thioglycolate, 1.3 g of potassium carbonate and 20 ml of DMF was stirred at 140° C. for hours, and then 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 848 mg of methyl 6-(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

出典と根拠

ORDレコード
ord-0247623088074d76875e4ab95f35e7c3
出典データセット
uspto-grants-2016_01
特許番号
US09232792B2

反応ノート

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