Methyl Thioglycolate → 6-Methoxy-benzo[B]thiophene-2-carboxylic acid methyl ester

HRID 493182Notes

Reaction equation

HRID 493182 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].F[C:8]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:9]=1[CH:10]=O>CS(C)=O>[CH3:6][O:5][C:1]([C:2]1[S:3][C:12]2[CH:13]=[C:14]([O:16][CH3:17])[CH:15]=[CH:8][C:9]=2[CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 16907Methyl ThioglycolateHCID 27348732-Fluoro-4-methoxybenzaldehyde

Product 1

HCID 534861116-Methoxy-benzo[B]thiophene-2-carboxylic acid methyl esterYield 65.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of methyl thioglycolate (1.29 mL, 14 mmol, 1.1 eq.) in 22 mL of DMSO was added Nail 50% (0.972 g, 20 mmol, 1.56 eq.) and the mixture was stirred for 5 Min., before 2-fluoro-4-methoxybenzaldehyde (2.00 g, 13 mmol) was added (strongly exothermic). When the internal temperature had reached again 25° C., the reaction mixture was poured onto crashed ice and the precipitate filtered off, washed with water, and dried to obtain 1.896 g of the title compound as light yellow crystals.

Workup

  1. customhad reached again 25° C.
  2. additionthe reaction mixture was poured
  3. filtrationthe precipitate filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-af06da65392f413abbb505d425405a06
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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