Sodium sulfide nonahydrate → 5-Fluoro-2-methyl-3-nitroaniline

HRID 1901249Notes

Reaction equation

HRID 1901249 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([N+:11]([O-])=O)[C:5]=1[CH3:14])([O-:3])=[O:2].O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+]>C(O)C.O>[NH2:11][C:6]1[CH:7]=[C:8]([F:10])[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=1[CH3:14]

Participants

5

Reactant 2

HCID 73972Sodium sulfide nonahydrateHCID 184653725-Fluoro-2-methyl-1,3-dinitrobenzene

Product 1

HCID 184653775-Fluoro-2-methyl-3-nitroaniline

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 2,6-dinitro-4-fluorotoluene (8.1 g) in ethanol (130 mL) is treated dropwise with a solution of sodium sulfide nonahydrate (16.39 g) in water (90 mL). The mixture is allowed to stir at room temperature for 2.5 hours, then diluted with water (500 mL) and extracted with ethyl acetate (4×500 mL). The combined extracts are dried over sodium sulfate and rotary evaporated. The residue is purified by flash chromatography on silica gel, eluting with 15% ethyl acetate/hexane to afford 2-amino-4-fluoro-6-nitrotoluene as a solid.

Workup

  1. extractionextracted with ethyl acetate (4×500 mL)
  2. dry with materialThe combined extracts are dried over sodium sulfate and rotary evaporated
  3. customThe residue is purified by flash chromatography on silica gel
  4. washeluting with 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-2c5a0b10c292411385032c36d48880b6
Source dataset
uspto-grants-1996_11
Patent number
US05576437

Reaction notes

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