Reaction #2358487

Reaction equation

2-fluoro-6-(trifluoromethyl)benzaldehyde

methyl thioglycolate

potassium carbonate

DMF

→

methyl 4-(trifluoromethyl)benzo[b]thiophene-2-carboxylate

Yield 35.4%

Solvents

water

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was cooled to room temperature
2. 2
   Extractionextracted with tert-butyl methyl ether 3 times
3. 3
   WashThe combined organic layer was washed with water
4. 4
   DryingThe mixture was dried over magnesium sulfate
5. 5
   Concentrationconcentrated under reduced pressure

Procedure

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).

Source