Nitric Acid → HCID 68650903, compound

HRID 1771900Notes

Reaction equation

HRID 1771900 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[N+:10]([O-])([OH:12])=[O:11]>OS(O)(=O)=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[CH3:9]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 679832,4-Difluoro-1-methylbenzene

Product 1

HCID 68650903HCID 68650903, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
45 °C

Procedure

To a stirred solution of 2,4-difluorotoluene (25.0 g, 195.3 mmol) in conc. H2SO4 (60 mL) was added fuming HNO3 (30 mL) drop wise at the rate that temperature was maintained between 40-50° C. over a period of 1.5 h. The reaction mixture was stirred at 40° C. for an additional 1 h. The reaction mixture was poured into ice-cold water (500 mL) and the solid precipitated was filtered and washed with water (2×50 mL). The solid residue was dissolved in EtOAc (200 mL), washed with aq. NaHCO3 (2×200 mL). The organic layer was dried over Na2SO4, filtered and evaporated in vacuo to afford 1,5-difluoro-2-methyl-3-nitrobenzene (21.0 g, 62%) as a light brown liquid.

Workup

  1. customthe solid precipitated
  2. filtrationwas filtered
  3. washwashed with water (2×50 mL)
  4. dissolutionThe solid residue was dissolved in EtOAc (200 mL)
  5. washwashed with aq. NaHCO3 (2×200 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-3f2dd4b2681b43fd998d8cd68801d34b
Source dataset
uspto-grants-2016_02
Patent number
US09249147B2

Reaction notes

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