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

HRID 453086Notes

Reaction equation

HRID 453086 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-0039ea76f04d43479f543eb039b05e88
Source dataset
uspto-grants-2013_07
Patent number
US08492411B2

Reaction notes

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