Sodium methanethiolate → Methyl 5-methylthio-2-nitrophenylacetate

HRID 1386312Notes

Reaction equation

HRID 1386312 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:7]=1.[CH3:16][S-:17].[Na+]>CS(C)=O>[CH3:16][S:17][C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:7]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolate2×HCID 15292019Methyl 2-(5-fluoro-2-nitrophenyl)acetate

Product 1

HCID 21717190Methyl 5-methylthio-2-nitrophenylacetateYield 81%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of methyl 5-fluoro-2-nitrophenylacetate (3 g, 14 mmol), (Synthesis 1993, 51), in DMSO (10 ml) was added to a suspension of sodium thiomethoxide (1.08 g, 15.5 mmol) in anhydrous DMSO (10 ml). The mixture was stirred for 10 minutes at ambient temperature and further sodium thiomethoxide (100 mg, 1.5 mmol) was added. The mixture was stirred for 15 minutes at ambient temperature and was then partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with ethyl acetate/petroleum ether (15/85) to give methyl 5-methylthio-2-nitrophenylacetate (2.68 g, 81%).

Workup

  1. stirringThe mixture was stirred for 15 minutes at ambient temperature
  2. customwas then partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customThe residue was purified by column chromatography
  8. washeluting with ethyl acetate/petroleum ether (15/85)

Sources & evidence

ORD record
ord-83eb2fe293424a4faf168608662bc061
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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