Pyridine → 4-Fluoro-2-(methylthio)-1-nitrobenzene

HRID 1971844Notes

Reaction equation

HRID 1971844 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].N1C=CC=CC=1.[CH3:18][S-:19].[Na+]>CO.ClCCl>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([S:19][CH3:18])[CH:7]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 679672,4-DifluoronitrobenzeneHCID 4378561Sodium methanethiolate

Product 1

HCID 127009124-Fluoro-2-(methylthio)-1-nitrobenzeneYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a mixture of compound 2,4-difluoro-1-nitro-benzene (10 g, 62.9 mmol), pyridine (10 ml, 124 mmol) in MeOH (30 ml) was added the solution of sodium thiomethoxide(20%, 300 mmol) in methanol drop-wise at 0° C. The mixture was stirred for 2 hour and then diluted with dichloromethane. The mixture was washed with brine, dried over MgSO4 and evaporated under reduced pressure. The resulting residue was recrystallized from ethyl acetate to give titled compound (10 g, yield 85%)

Workup

  1. washThe mixture was washed with brine
  2. dry with materialdried over MgSO4
  3. customevaporated under reduced pressure
  4. customThe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-558185119e5a460bb5fb067f8dc8058a
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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