Nitric Acid → 5-Fluoro-2-methyl-1,3-dinitrobenzene

HRID 1477838Notes

Reaction equation

HRID 1477838 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:7]=[C:6]([N+:12]([O-:14])=[O:13])[C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 679654-Fluoro-2-nitrotoluene

Product 1

HCID 184653725-Fluoro-2-methyl-1,3-dinitrobenzene

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

Fuming sulphuric acid (105 mL) was added dropwise to 4-fluoro-1-methyl-2-nitrobenzene (30 g, 0.194 mol) at −5° C. 0° C. and a mixture of fuming sulphuric acid (54 mL) and fuming nitric acid (18 mL) was added dropwise to it at −5° C. 0° C. over the period of 3 h. After complete addition, the reaction mixture was stirred for 3 hours at ambient temperature. TLC showed complete conversion of starting material to the product. The reaction mixture was poured into ice and extracted with dichloromethane. The combined organic layers was washed with water (600 mL), sat. sodium bicarbonate (600 mL) and brine (600 mL). It was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the crude product, which was purified by silica gel column chromatography (PE: EA=20:1) to afford the title compound.

Workup

  1. additionwas added dropwise to it at −5° C
  2. custom0° C.
  3. customover the period of 3 h
  4. additionAfter complete addition
  5. additionThe reaction mixture was poured into ice
  6. extractionextracted with dichloromethane
  7. washThe combined organic layers was washed with water (600 mL), sat. sodium bicarbonate (600 mL) and brine (600 mL)
  8. dry with materialIt was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customto give the crude product, which
  11. customwas purified by silica gel column chromatography (PE: EA=20:1)

Sources & evidence

ORD record
ord-b6e24dbbc6544990a219a3fffcbf1c2c
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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