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

HRID 589283Notes

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

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 obtain 480 mg of methyl 4-(trifluoromethyl)benzo[b]thiophene-2-carboxylate.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with tert-butyl methyl ether 3 times
washThe combined organic layer was washed with water
dry with materialThe mixture was dried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-3eecd179de074839a2f5d6da214e2a65
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09232792B2

Reaction notes

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