Methyl Thioglycolate → Methyl 7-(trifluoromethyl)-1-benzothiophene-2-carboxylate

HRID 15432Notes

Reaction equation

F[C:2]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[H-].[Na+].[SH:16][CH2:17][C:18]([O:20][CH3:21])=[O:19]>>[CH3:21][O:20][C:18]([C:17]1[S:16][C:2]2[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=1)=[O:19]

Participants

Reactant 3

HCID 16907Methyl Thioglycolate

HCID 24758Sodium hydride

HCID 5179782-Fluoro-3-(trifluoromethyl)benzaldehyde

Product 1

HCID 18526203Methyl 7-(trifluoromethyl)-1-benzothiophene-2-carboxylate

Procedure

Using 5.0 g (26.0 mmol) of 2-fluoro-3-trifluoromethylbenzaldehyde, 1.56 g (39.0 mmol) of sodium hydride (60% pure) and 3.0 g (28.6 mmol) of methyl mercaptoacetate, 5.4 g (79.7% of theory) of the title compound are obtained.

Sources & evidence

ORD record: ord-9532cc4e02a445268bce4d2003462fad
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732477B2

Reaction notes

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