Methyl Thioglycolate → 6-Bromo-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 658160

Reaction equation

[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4](F)[CH:3]=1.[H-].[Na+].[SH:13][CH2:14][C:15]([O:17][CH3:18])=[O:16]>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]2[CH:6]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[S:13][C:4]=2[CH:3]=1

Participants

Reactant 3

HCID 16907Methyl Thioglycolate

HCID 24758Sodium hydride

HCID 1435174-Bromo-2-fluorobenzaldehyde

Product 1

HCID 224740786-Bromo-benzo[b]thiophene-2-carboxylic acid methyl ester

Procedure

Using 6.54 g (32.2 mmol) of 4-bromo-2-fluorobenzaldehyde, 1.93 g (48.3 mmol) of sodium hydride (60% pure) and 3.76 g (35.5 mmol) of methyl mercaptoacetate, 4.06 g (46.4% of theory) of the title compound are obtained.

Sources & evidence

ORD record: ord-f8131eb86a6949a48d5cb06477996205
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076355B2

Linked notes

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