Sodium Carbonate → 5-(2-Chloro-phenyl)-thiophene-2-carbaldehyde

HRID 1394152Notes

Reaction equation

HRID 1394152 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.[CH:9]([C:11]1[S:15][C:14](B(O)O)=[CH:13][CH:12]=1)=[O:10].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OC(=O)C)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:14]1[S:15][C:11]([CH:9]=[O:10])=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 119931-Chloro-2-iodobenzeneHCID 27734305-Formyl-2-thiopheneboronic acid

Product 1

HCID 35780575-(2-Chloro-phenyl)-thiophene-2-carbaldehyde

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-1-iodobenzene (0.25 mL) and 5-formyl-2-thiophene boronic acid (0.385 g) in DME (8 mL) were added Pd(OAc)2 (0.009 g) and Ph3P (0.021 g) followed by 2M sodium carbonate (1 mL). The mixture was stirred at rt for 1 h. The reaction was diluted with ethylacetate (20 mL) and washed with water and brine, and then dried (sodium sulfate). The crude product was purified by flash-chromatography using EtOAc-hexanes (1:5) to give the desired 5-(2-chlorophenyl)thiophene-2-aldehyde as an oil. The aldehyde (0.15 g), thus obtained, was then condensed with 2,4-thiazolidine-2,4dione in the presence of benzoic acid and piperidine under the conditions described in EXAMPLE 5 to give the title compound 5-(5-(2-chloro-phenyl)thienylidene)thiazolidine-2,4-dione.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (sodium sulfate)
  3. customThe crude product was purified by flash-chromatography

Sources & evidence

ORD record
ord-c3920f85766e49f6a81c9a6e1885e28f
Source dataset
uspto-grants-2008_03
Patent number
US07348348B2

Reaction notes

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