Methyl Thioglycolate → Methyl 5-fluoro-1-benzothiophene-2-carboxylate

HRID 15435

Reaction equation

F[C:2]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=1[CH:4]=O.[H-].[Na+].[SH:13][CH2:14][C:15]([O:17][CH3:18])=[O:16]>>[CH3:18][O:17][C:15]([C:14]1[S:13][C:2]2[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:3]=2[CH:4]=1)=[O:16]

Participants

Reactant 3

HCID 16907Methyl Thioglycolate

HCID 24758Sodium hydride

HCID 1376632,5-Difluorobenzaldehyde

Product 1

HCID 22473847Methyl 5-fluoro-1-benzothiophene-2-carboxylate

Procedure

Using 5.0 g (35.2 mmol) of 2,5-difluorobenzaldehyde, 2.11 g (52.78 mmol) of sodium hydride (60% pure) and 4.11 g (38.7 mmol) of methyl mercaptoacetate, 1.1 g (14.3% of theory) of the title compound are obtained.

Sources & evidence

ORD record: ord-28aaadee87cc4a78bb55ccfaafe7e468
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732477B2

Linked notes

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