1,2-Difluoro-4-nitrobenzene → 2-Fluoro-4-nitrothioanisole

HRID 1931561Notes

Reaction equation

HRID 1931561 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[CH3:12][S-:13].[Na+]>O>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[S:13][CH3:12]

Participants

4

Reactant 2

HCID 1230531,2-Difluoro-4-nitrobenzeneHCID 4378561Sodium methanethiolate

Product 1

HCID 225925052-Fluoro-4-nitrothioanisoleYield 66.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3,4-difluoro-nitrobenzene (25 g, 0.157 mol) and sodium methanethiolate (10.5 g, 0.15 mol) was stirred at room temperature overnight. The reaction mixture was poured into water and extracted twice with ether. The extracts were combined, washed with water (twice) and brine, dried (sodium sulfate), filtered, evaporated, and purified by column chromatography, eluting with 17% dichloromethane/hexanes to give 2-fluoro-1-methylsulfanyl-4-nitro-benzene (18.6 g, 63%).

Workup

  1. extractionextracted twice with ether
  2. washwashed with water (twice) and brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by column chromatography
  7. washeluting with 17% dichloromethane/hexanes

Sources & evidence

ORD record
ord-f4dccd07149a4d5fa93b52fe4c9653a9
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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