Реакция #2358486

ord-111c605a61134ec3ae46115e80cc1207

Уравнение реакции

O=Cc1ccc(C(F)(F)F)cc1F
2-fluoro-4-(trifluoromethyl)benzaldehyde
COC(=O)CS
methyl thioglycolate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CN(C)C=O
DMF
COC(=O)c1cc2ccc(C(F)(F)F)cc2s1
methyl-6-(trifluoromethyl)benzo[b]thiophene-2-carboxylate
Выход 56.4%

Растворители

Условия реакции

Температура
140°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Температураthe reaction mixture was cooled to room temperature
  2. 2
    Экстракцияextracted with tert-butyl methyl ether 3 times
  3. 3
    ПромывкаThe combined organic layer was washed with water
  4. 4
    СушкаThe mixture was dried over magnesium sulfate
  5. 5
    Концентрированиеconcentrated under reduced pressure

Методика

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 2 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 (the present compound 2).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US09119396B2uspto-grants-2015_09