Methyl Thioglycolate → 5,7-Difluoro-benzo[B]thiophene-2-carboxylic acid methyl ester

HRID 658166Notes

Reaction equation

F[C:2]1[C:9]([F:10])=[CH:8][C:7]([F:11])=[CH:6][C:3]=1[CH:4]=O.[H-].[Na+].[SH:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]>>[F:11][C:7]1[CH:8]=[C:9]([F:10])[C:2]2[S:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:4][C:3]=2[CH:6]=1

Participants

Reactant 3

HCID 16907Methyl Thioglycolate

HCID 24758Sodium hydride

HCID 27769502,3,5-Trifluorobenzaldehyde

Product 1

HCID 573508905,7-Difluoro-benzo[B]thiophene-2-carboxylic acid methyl ester

Procedure

Using 3.94 g (24.6 mmol) of 2,3,5-trifluorobenzaldehyde, 1.48 g (36.9 mmol) of sodium hydride (60% pure) and 2.88 g (27.1 mmol) of methyl mercaptoacetate, 3.58 g (56% of theory) of the title compound are obtained in a purity of 89%. Recrystallization from methanol gives the product in a purity of 97%.

Sources & evidence

ORD record: ord-c507435735974594b27984ee37094429
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076355B2

Reaction notes

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