Dimethylformamide → 4-Chloro-2-(methylthio)benzaldehyde

HRID 910874Notes

Reaction equation

HRID 910874 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1C=O.[CH3:11][S-:12].[Na+].CN([CH:17]=[O:18])C>O>[Cl:1][C:2]1[CH:3]=[CH:6][C:7]([CH:17]=[O:18])=[C:8]([S:12][CH3:11])[CH:9]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 4378561Sodium methanethiolate

Product 1

HCID 190766934-Chloro-2-(methylthio)benzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

The subtitle compound was prepared by using 2-chloro-4-fluorobenzaldehyde (1.16 g) in dry DMF (20 ml). The mixture was treated with sodium thiomethoxide (0.52 g) and heated to 50° C. for 2 hours. The mixture was diluted with water, extracted with ethyl acetate, dried and concentrated under reduced pressure to give a solid. The residue was purified by chromatography on silica eluting with isohexane/diethylether 2:1 to give a white solid, yield 0.70 g.

Workup

  1. extractionextracted with ethyl acetate
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customto give a solid
  5. customThe residue was purified by chromatography on silica eluting with isohexane/diethylether 2:1
  6. customto give a white solid, yield 0.70 g

Sources & evidence

ORD record
ord-4cd3fac65bf5437cba65cda14e5e38d1
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

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