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

HRID 1691609Notes

Reaction equation

HRID 1691609 reaction equation
[H-].[Na+].[SH:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[H][H].[Br:11][C:12]1[C:13](F)=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=O>CS(C)=O>[Br:11][C:12]1[C:13]2[S:3][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:15][C:14]=2[CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 16907Methyl ThioglycolateHCID 24758Sodium hydrideHCID 220193613-Bromo-2-fluorobenzaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 18526159Methyl 7-bromobenzo[b]thiophene-2-carboxylateYield 55.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Under an argon atmosphere, 8.2 g (205.7 mmol) of sodium hydride (60% in liquid paraffin) are introduced into 300 ml of absolute DMSO. At room temperature, 16.0 g (150.9 mmol) of methyl mercaptoacetate are slowly added dropwise to the reaction mixture, which is stirred at room temperature until hydrogen evolution ceases (about 15 min). A solution of 27.8 g (137.1 mmol) of 3-bromo-2-fluorobenzaldehyde in 50 ml of absolute DMSO is added at room temperature to the reaction mixture. The latter is stirred until the reaction is complete and then poured into ice-water. The resulting precipitate is filtered off with suction and dried in vacuo at 40° C. overnight. 20.57 g of a mixture of the title compound and of the corresponding acid (approx. 1:1) are obtained.

Workup

  1. filtrationThe resulting precipitate is filtered off with suction
  2. customdried in vacuo at 40° C. overnight

Sources & evidence

ORD record
ord-eed5ef8650b34f9fb1b228a033357132
Source dataset
uspto-grants-2012_04
Patent number
US08153799B2

Reaction notes

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