Potassium Carbonate → Methyl 6-chloro-1-benzothiophene-2-carboxylate

HRID 2243178Notes

Reaction equation

HRID 2243178 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([N+]([O-])=O)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:19]([O:23][CH3:24])(=[O:22])[CH2:20][SH:21]>CN(C=O)C>[CH3:24][O:23][C:19]([C:20]1[S:21][C:4]2[CH:3]=[C:2]([Cl:1])[CH:9]=[CH:8][C:5]=2[CH:6]=1)=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 796744-Chloro-2-nitrobenzaldehyde

Product 1

HCID 18526200Methyl 6-chloro-1-benzothiophene-2-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 600 mg (3.23 mmol) of 4-chloro-2-nitro-benzaldehyde in DMF (7 ml) were added 559 mg (4.04 mmol) of potassium carbonate and 294 μl (3.23 mmol) of methyl thioglycolate at 0° C. The reaction mixture was stirred for 30 min at 0° C. and then for 24 h at RT. Then the mixture was poured into ice-water and the precipitate was collected by filtration and dissolved in ethyl acetate. The solution was dried (MgSO4) and concentrated to yield 630 mg (86%) of 6-chloro-benzo[b]thiophene-2-carboxylic acid methyl ester as a white solid. 1HNMR (CDCl3, 300 MHz): δ 3.95 (s, 3H), 7.88 (dd, J=8.6 and 1.9 Hz, 1H), 7.79 (d, J=8.6 Hz, 1H), 7.85 (d, J=1.9 Hz, 1H), 8.02 (s, 1H).

Workup

  1. waitfor 24 h at RT
  2. filtrationthe precipitate was collected by filtration
  3. dissolutiondissolved in ethyl acetate
  4. dry with materialThe solution was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a0b95c4f6cf44a61887225a6504f7b86
Source dataset
uspto-grants-2010_03
Patent number
US07674815B2

Reaction notes

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