Dimethylformamide → 4-Chloro-2-ethylsulfanylbenzaldehyde

HRID 521666

Reaction equation

HRID 521666 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4](F)[CH:3]=1.[CH2:11]([SH:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([S:13][CH2:11][CH3:12])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 27249084-Chloro-2-fluorobenzaldehyde

Product 1

HCID 1148635404-Chloro-2-ethylsulfanylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.0 g of 4-chloro-2-fluorobenzaldehyde, 2.05 ml of ethanethiol, 3.82 g of potassium carbonate and 6 ml of DMF was stirred at room temperature for 6 hours, and was allowed to stand overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 3.57 g of 4-chloro-2-ethylsulfanylbenzaldehyde.

Workup

  1. waitto stand overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3ecac01b7d224c75b9a09b7aa985bcb2
Source dataset
uspto-grants-2016_05
Patent number
US09328121B1

Linked notes

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