5-Fluoro-2-nitroanisole → (3-methoxy-4-nitrophenyl)(methyl)sulfane(WX191877)

HRID 2283508Notes

Reaction equation

HRID 2283508 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[CH3:13][S-:14].[Na+]>CN(C=O)C.O>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([S:14][CH3:13])[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 27792505-Fluoro-2-nitroanisoleHCID 4378561Sodium methanethiolate

Product 1

HCID 86688022(3-methoxy-4-nitrophenyl)(methyl)sulfane(WX191877)Yield 59.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-fluoro-2-methoxy-1-nitrobenzene (1.38 g, 8.06 mmol) and sodium methyl mercaptide (0.622 g, 8.87 mmol) in DMF (25 mL) was stirred at room temperature for 18 hours. The reaction was the diluted with water and extracted with EtOAc. The combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to give (3-methoxy-4-nitrophenyl)(methyl)sulfane (0.95 g, 59%).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-86ecef930b4c4432b501cd96b42cc925
Source dataset
uspto-grants-2015_09
Patent number
US09145402B2

Reaction notes

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