Dimethylformamide → Methyl 7-chlorobenzo[b]thiophene-2-carboxylate

HRID 2183647Notes

Reaction equation

HRID 2183647 reaction equation
[CH3:1][CH:2]([SH:6])[C:3]([O-:5])=[O:4].[Cl:7][C:8]1[C:9](F)=[C:10]([CH:13]=[CH:14][CH:15]=1)C=O.[CH3:17]N(C)C=O>>[Cl:7][C:8]1[C:9]2[S:6][C:2]([C:3]([O:5][CH3:17])=[O:4])=[CH:1][C:10]=2[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 7363353-Chloro-2-fluorobenzaldehydeHCID 156077362-Mercaptopropionate

Product 1

HCID 22474203Methyl 7-chlorobenzo[b]thiophene-2-carboxylate

Procedure

In a similar manner to Example 18, methylthioglycolate (13 g) was reacted with 3-chloro-2-fluorobenzaldehyde (19.57 g) in dimethylformamide to give methyl 7-chlorobenzo[b]thiophene-2-carboxylate, which was hydrolysed, chlorinated and reacted with N,O-dimethylhydroxylamine hydrochloride to give 7-chloro-N-methoxy-N-methylbenzo[b]thiophene-2-carboxamide, which was reacted with ethylmagnesium bromide to give 1-(7-chlorobenzo[b]thiophen-2-yl)propan-1-one. This ketone (1.17 g) was reacted with phenyltrimethylammonium tribromide (2.15 g) to give 2-bromo-1-(7-chlorobenzo[b]thiophen-2-yl)propan-1-one (2.32 g) which was used without further purification.

Sources & evidence

ORD record
ord-1de7951e465f4c72ad4cecc759e1e5bd
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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