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

HRID 1621023Notes

Reaction equation

HRID 1621023 reaction equation
[H-].[Na+].[SH:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[H][H].[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[C:14](F)[CH:13]=1>CS(C)=O>[Br:11][C:12]1[CH:19]=[CH:18][C:15]2[CH:16]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[S:3][C:14]=2[CH:13]=1

Participants

6

Reactant 4

HCID 16907Methyl ThioglycolateHCID 24758Sodium hydrideHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Under an argon atmosphere, 1.93 g (48.3 mmol) of sodium hydride (60% in liquid paraffin) are introduced into 60 ml of absolute DMSO. At room temperature, 3.76 g (35.5 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 6.54 g (32.2 mmol) of 4-bromo-2-fluorobenzaldehyde and 15 ml of absolute DMSO are 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. 4.06 g (46.4% of theory) of the title compound are obtained.

Workup

  1. additionare added at room temperature to the reaction mixture
  2. filtrationThe resulting precipitate is filtered off with suction
  3. customdried in vacuo at 40° C. overnight

Sources & evidence

ORD record
ord-fd6073a8ada4420fb8e6807dd635ae73
Source dataset
uspto-grants-2014_07
Patent number
US08772511B2

Reaction notes

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