Methyl iodide → Methyl 2-(4-(methylthio)phenyl)acetate

HRID 505883Notes

Reaction equation

HRID 505883 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[C:13]([O-])(O)=O.[Na+].IC>CN(C=O)C>[CH3:13][O:11][C:10](=[O:12])[CH2:9][C:6]1[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 49839124-(Methylthio)phenylacetic acid

Product 1

HCID 12067662Methyl 2-(4-(methylthio)phenyl)acetateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.82 g (10 mmol) of the 4-methylthiophenylacetic acid were dissolved in 30 mL of DMF and 1.34 g (16 mmol) of NaHCO3 are then added; the agitation mixture is stirred for 15 min approx. Next, 1.9 mL of ICH3 are added while keeping agitation at room temperature for 24 h. Once this time elapsed the mixture is poured on water/ice. As no precipitation occurs ether is added and extracted. The organic phase is washed with water and after drying on sodium sulfate anhydride, the organic phase is concentrated in a rotary evaporator getting 1.92 g (9.7 mmol, 97% yield) of colorless oil which spectroscopic data confirm the expected structure. This product will be used in the next step of the synthesis process without purification as it provides a single stain in TLC (eluting dichloromethane/methanol 9/1).

Workup

  1. customat room temperature
  2. customfor 24 h
  3. additionis poured on water/ice
  4. customAs no precipitation
  5. additionis added
  6. extractionextracted
  7. washThe organic phase is washed with water
  8. customafter drying on sodium sulfate anhydride
  9. concentrationthe organic phase is concentrated in a rotary evaporator

Sources & evidence

ORD record
ord-0b25af229efc46c7a0c16a34b36e92b5
Source dataset
uspto-grants-2010_08
Patent number
US07781594B2

Reaction notes

Loading…