Methyl Thioglycolate → Methyl 7-bromobenzo[b]thiophene-2-carboxylate

Reaction equation

[Br:1][C:2]1[C:3](F)=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=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:3]2[C:2]([Br:1])=[CH:9][CH:8]=[CH:7][C:4]=2[CH:5]=1)=[O:16]

Participants

Reactant 3

HCID 16907Methyl Thioglycolate

HCID 24758Sodium hydride

HCID 220193613-Bromo-2-fluorobenzaldehyde

Product 1

HCID 18526159Methyl 7-bromobenzo[b]thiophene-2-carboxylate

Procedure

Using 27.8 g (137.1 mmol) of 3-bromo-2-fluorobenzaldehyde, 8.2 g (205.7 mmol) of sodium hydride (60% pure) and 16.0 g (150.9 mmol) of methyl mercaptoacetate, 20.57 g of a mixture of the title compound and the corresponding acid (about 1:1) are obtained.

Sources & evidence

ORD record: ord-c70fc1add407400192318d4fd26d8681
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732477B2

Reaction notes

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