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

HRID 2183682Notes

Reaction equation

HRID 2183682 reaction equation
S1C=CC2C=CC(C(=O)CC)=CC1=2.[C:14]([O:18][CH3:19])(=[O:17])[CH2:15][SH:16].[Br:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[C:23](F)[CH:22]=1>>[Br:20][C:21]1[CH:22]=[CH:23][C:24]2[CH:25]=[C:15]([C:14]([O:18][CH3:19])=[O:17])[S:16][C:27]=2[CH:28]=1

Participants

4

Reactant 3

HCID 16907Methyl ThioglycolateHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 22474194HCID 22474194, compound

Product 1

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

Procedure

In a similar manner to Example 9 Method A, 1-(benzo[b]thiophen-6-yl)propan-1-one was prepared starting from methyl thioglycolate (17.8 ml) and 4-bromo-2-fluorobenzaldehyde (40 g) which were reacted together to give methyl 6-bromobenzo[b]thiophene-2-carboxylate (55 g), m.p. 108-110° C. This ester was hydrolysed to give 6-bromobenzo[b]thiophene-2-carboxylic acid (48 g), which was decarboxylated using copper and quinoline at 180-200° C. for 2 hours to give 6-bromobenzo[b]thiophene (20.3 g), m.p. 53-55° C. This compound (7.5 g) was reacted with magnesium (0.9 g) and then with N-methoxy-N-methylpropionamide (6.1 g) to give 1-(benzo[b]thiophen-6-yl)propan-1-one (3.6 g) as a pale yellow solid which was used without further purification.

Workup

  1. customwere reacted together

Sources & evidence

ORD record
ord-2c75dd6841b2471cad6da6a02f05749b
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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