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

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

Participants

Reactant 3

HCID 16907Methyl Thioglycolate

HCID 24758Sodium hydride

HCID 27349042-Fluoro-5-(trifluoromethyl)benzaldehyde

Product 1

HCID 14779565-Trifluoromethyl-benzo[b]thiophene-2-carboxylic acid methyl ester

Procedure

Using 4.28 g (22.3 mmol) of 2-fluoro-5-trifluoromethylbenzaldehyde, 1.34 g (33.4 mmol) of sodium hydride (60% pure) and 2.6 g (24.5 mmol) of methyl mercaptoacetate, 4.93 g (80.0% of theory) of the title compound are obtained.

Sources & evidence

ORD record: ord-957c2736ed1b4b33b685a55e2148c79e
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076355B2

Reaction notes

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