Methyl Thioglycolate → 5-Bromo-benzo(b)thiophene-2-carboxylic acid

HRID 2183650Notes

Reaction equation

HRID 2183650 reaction equation
S1C=CC2C=C(C(=O)CC)C=CC1=2.[C:14]([O:18]C)(=[O:17])[CH2:15][SH:16].[Br:20][C:21]1[CH:22]=[CH:23][C:24](F)=[C:25]([CH:28]=1)[CH:26]=O>>[Br:20][C:21]1[CH:22]=[CH:23][C:24]2[S:16][C:15]([C:14]([OH:18])=[O:17])=[CH:26][C:25]=2[CH:28]=1

Participants

4

Reactant 3

HCID 16907Methyl ThioglycolateHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 22473806HCID 22473806, compound

Product 1

HCID 7377375-Bromo-benzo(b)thiophene-2-carboxylic acidYield 95.1%

Procedure

In a similar manner to Example 9 Method A, 1-(benzo[b]thiophen-5-yl)propan-1-one was prepared starting from methyl thioglycolate (13.2 g) and 5-bromo-2-fluorobenzaldehyde (25.35 g) which were reacted together and the product hydrolysed to give 5-bromobenzo[b]thiophene-2-carboxylic acid (30.4 g), which was decarboxylated using copper and quinoline at 190° C. for 1.5 hours to give 5-bromobenzo[b]thiophene. This compound was reacted with magnesium and then with N-methoxy-N-methylpropionamide to give 1-(benzo[b]thiophen-5-yl)propan-1-one (1.3 g) as a cream solid which was used without further purification.

Workup

  1. customwere reacted together

Sources & evidence

ORD record
ord-a90a08eefb3b435c8c654d17780a8d6f
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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