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

HRID 658171Notes

Reaction equation

Cl[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[H-].[Na+].[SH:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]>>[N+:10]([C:9]1[C:2]2[S:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:4][C:3]=2[CH:6]=[CH:7][CH:8]=1)([O-:12])=[O:11]

Participants

Reactant 3

HCID 16907Methyl Thioglycolate

HCID 24758Sodium hydride

HCID 126677132-Chloro-3-nitrobenzaldehyde

Product 1

HCID 57722418Methyl 7-nitrobenzo[b]thiophene-2-carboxylate

Procedure

Using 3.04 g (16.4 mmol) of 2-chloro-3-nitrobenzaldehyde, 0.98 g (24.6 mmol) of sodium hydride (60% pure) and 2.09 g (19.7 mmol) of methyl mercaptoacetate, 3.68 g (85% of theory) of the title compound are obtained.

Sources & evidence

ORD record: ord-665d0357313742e4b70d9bef1e86d8e2
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076355B2

Reaction notes

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