Nitric Acid → 1-Methyl-2-nitro-3-(trifluoromethyl)benzene

HRID 358416Notes

Reaction equation

HRID 358416 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:6][CH:7]=1.[N+:12]([O-])([OH:14])=[O:13].O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[N+:12]([C:3]1[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=1[C:8]([F:9])([F:10])[F:11])([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 1362463-MethylbenzotrifluorideHCID 516892Sodium Bicarbonate

Product 1

HCID 134554311-Methyl-2-nitro-3-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
15 °C

Procedure

2 gms of 3-methyl benzotrifluoride is dissolved in 5 mls of methylene chloride and added dropwise with stirring at -20° C. to -25° C. to 6 gms of 98% HNO3 dissolved in 10 ml methylene chloride. After addition, the reaction was allowed to finish by warming the mixture to 15° C. After treatment with ice and water followed by sodium bicarbonate wash, near quantitative yield was recovered. Isomer distribution was as follows:

Workup

  1. additionadded dropwise
  2. additionAfter addition
  3. washwash, near quantitative yield
  4. customwas recovered

Sources & evidence

ORD record
ord-5b33dbfb87f8438d8104f2a811283c5e
Source dataset
uspto-grants-1984_08
Patent number
US04467125

Reaction notes

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