Dimethyl Sulfoxide → HCID 68537107, compound

HRID 644268Notes

Reaction equation

HRID 644268 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH2:13][O:14][CH3:15])[CH:3]=1.CS(C)=O.[CH2:20]([S-:22])[CH3:21].[Na+]>O>[CH2:20]([S:22][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH2:13][O:14][CH3:15])[CH:3]=1)[CH3:21]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 4459711Sodium ethanethiolateHCID 58437341Methyl 4-fluoro-2-(methoxymethoxy)benzoate

Product 1

HCID 68537107HCID 68537107, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 4-fluoro-2-(methoxymethoxy)benzoate (10.6 g, 50 mmol) and DMSO (20 mL), under nitrogen, was added sodium ethanethiolate (5.8 g, 55 mmol) in portions. The exothermic reaction was stirred for 19 h, diluted with water, and extracted with ethyl acetate. The organic layer was concentrated; and the residue was dissolved in ether, filtered through diatomaceus earth, and concentrated to give intermediate methyl 4-(ethylthio)-2-(methoxymethoxy)benzoate.

Workup

  1. customThe exothermic reaction
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. dissolutionand the residue was dissolved in ether
  5. filtrationfiltered through diatomaceus earth
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d0e303483cf64d2d85a34241994a09d2
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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