2-Chlorobenzaldehyde → HCID 10636680, compound

HRID 1872589Notes

Reaction equation

HRID 1872589 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[SH:9].C(=O)([O-])[O-].[K+].[K+].Cl[C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=[O:20]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=[O:20]

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 11430Potassium CarbonateHCID 707302,4-Dichlorobenzenethiol

Product 1

HCID 10636680HCID 10636680, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 2,4-dichlorothiophenol (2.0 g, 11.2 mmol) in 25 mL of anhydrous DMF was added potassium carbonate (3.09 g, 22.4 mmol), followed by 2-chlorobenzaldehyde (1.26 mL, 11.3 mmol). The mixture was then heated under nitrogen atmosphere at 70° C. for 5 hours. The reaction mixture was then allowed to cool to room temperature and partitioned between ether and water. The aqueous layer was extracted with ether once and the combined organic layer was washed with water and brine, dried over sodium sulfate and condensed in vacuo. The crude product was purified via silica gel flash chromatography, eluting with 5-10% ether/hexanes, to give 2.62 g (9.25 mmol, 83%) of the desired aldehyde as a colorless oil, which solidified slowly upon standing at room temperature.

Workup

  1. temperatureto cool to room temperature
  2. custompartitioned between ether and water
  3. extractionThe aqueous layer was extracted with ether once
  4. washthe combined organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate and condensed in vacuo
  6. customThe crude product was purified via silica gel flash chromatography
  7. washeluting with 5-10% ether/hexanes

Sources & evidence

ORD record
ord-a0ca185f0058497da99b697558d8a2d9
Source dataset
uspto-grants-2000_08
Patent number
US06110922

Reaction notes

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