Potassium Hydroxide → 7-Chloro-5-nitro-benzo[b]thiophene-2-carboxylic acid methyl ester

HRID 1892058Notes

Reaction equation

HRID 1892058 reaction equation
Cl[C:2]1[C:9]([Cl:10])=[CH:8][C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]=1[CH:4]=O.[SH:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].[OH-].[K+]>CN(C=O)C.O>[CH3:19][O:18][C:16]([C:15]1[S:14][C:2]2[C:9]([Cl:10])=[CH:8][C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:3]=2[CH:4]=1)=[O:17]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 16907Methyl ThioglycolateHCID 187671622,3-Dichloro-5-nitrobenzaldehyde

Product 1

HCID 687278157-Chloro-5-nitro-benzo[b]thiophene-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,3-dichloro-5-nitrobenzaldehyde (10 g, 0.045 mol) and methyl mercaptoacetate (6.6 mL, 0.06 mol) in DMF (200 mL) was added KOH (6 g) in 50 mL water. After stirring for 2 h, the reaction mixture was poured in ice cold water and the mixture was extracted in ethyl acetate. The organic layer was washed with water and dried. The evaporation of the solvent gave crude product which was purified by repetitive washing with hexane to yield 7-chloro-5-nitro-benzo[b]thiophene-2-carboxylic acid methyl ester, 12.3 g.

Workup

  1. additionthe reaction mixture was poured in ice cold water
  2. extractionthe mixture was extracted in ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. customThe evaporation of the solvent
  6. customgave crude product which
  7. customwas purified
  8. washby repetitive washing with hexane

Sources & evidence

ORD record
ord-0ae3d05200c341128dacda76decd064b
Source dataset
uspto-grants-2013_08
Patent number
US08507509B2

Reaction notes

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