Nitric Acid → HCID 21472726, compound

HRID 2295053Notes

Reaction equation

HRID 2295053 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>[N+:9]([C:4]1[C:3]([N+:12]([O-:14])=[O:13])=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[CH3:8])([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 679654-Fluoro-2-nitrotoluene

Product 1

HCID 21472726HCID 21472726, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

Fuming sulfuric acid (180 mL) is added dropwise to 4-fluoro-2-nitrotoluene (50.21 g) under an argon atmosphere. The internal temperature of the mixture is maintained at 0°-5° C. using an ice/sodium chloride bath. A preformed (ice bath) mixture of fuming nitric acid (30 mL) and fuming sulfuric acid (90 mL) is added dropwise to the previous solution over three hours. The reaction is then allowed to warm to room temperature. After stirring at room temperature for two hours, the mixture is poured slowly into ice and the products are extracted with methylene chloride (4×500 mL). The combined extracts are dried over magnesium sulfate, filtered and rotary evaporated. The crude product is purified by flash chromatography on silica gel, eluting with 5% ethyl acetate/hexane to afford 2,3-dinitro-4-fluorotoluene as a pale yellow solid.

Workup

  1. temperatureThe internal temperature of the mixture is maintained at 0°-5° C.
  2. additionis added dropwise to the previous solution over three hours
  3. additionthe mixture is poured slowly into ice
  4. extractionthe products are extracted with methylene chloride (4×500 mL)
  5. dry with materialThe combined extracts are dried over magnesium sulfate
  6. filtrationfiltered
  7. customThe crude product is purified by flash chromatography on silica gel
  8. washeluting with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-f6058f4bddbd44baa44b37d2670cf46c
Source dataset
uspto-grants-1997_11
Patent number
US05691370

Reaction notes

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