Dimethylformamide → 5-Trifluoromethyl-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 1504574Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 5.0 g of 2-fluoro-5-(trifluoromethyl)benzaldehyde, 3.3 g of methyl thioglycolate, 4.0 g of potassium carbonate and 50 ml of DMF was stirred at 60° C. for 2 hours. The reaction mixture was cooled down to room temperature. To the reaction mixture was added water, and the mixture was extracted with tert-butyl methyl ether three times. The combined organic layers were washed with water and saturated saline, and dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was recrystallized from methanol, to obtain 6.3 g of methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate (present condensed ring compound 1).

Workup

temperatureThe reaction mixture was cooled down to room temperature
extractionthe mixture was extracted with tert-butyl methyl ether three times
washThe combined organic layers were washed with water and saturated saline
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was recrystallized from methanol

Sources & evidence

ORD record: ord-fd25db7c7d2241aaa240c5ada7d81532
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09215871B2

Reaction notes

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