Methyl Thioglycolate → methyl 5-bromo-1-benzothiophene-2-carboxylate

HRID 1012697Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=O.[H-].[Na+].[SH:13][CH2:14][C:15]([O:17][CH3:18])=[O:16]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:7][C:6]=2[CH:9]=1

Participants

Reactant 3

HCID 16907Methyl Thioglycolate

HCID 24758Sodium hydride

HCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 2824065methyl 5-bromo-1-benzothiophene-2-carboxylate

Procedure

Starting from 2.99 g (14.7 mmol) of 5-bromo-2-fluorobenzaldehyde, by general method A with 0.88 g (22.1 mmol) of sodium hydride (60%) and 1.72 g (16.2 mmol) of methyl mercaptoacetate, 2.76 g (69.1% of theory) of the title compound are obtained.

Sources & evidence

ORD record: ord-1844ad5880e14fc1a724522f78d65182
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977485B2

Reaction notes

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