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

HRID 658164Notes

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

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-ab926d66317645d48b023bfc95f030d6
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076355B2

Reaction notes

Loading…