Nitric Acid → 4-Fluoro-2-nitrotoluene

HRID 376441

Reaction equation

HRID 376441 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[N+:9]([O-])([OH:11])=[O:10].S(=O)(=O)(O)O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 9603p-Fluorotoluene

Product 1

HCID 679654-Fluoro-2-nitrotolueneYield 81.1%

Conditions

Temperature
100 °C

Procedure

4-Fluorotoluene (14 g) is added slowly with stirring to a solution of fuming nitric acid (18 g) and concentrated sulfuric acid (30 g) over 30 minutes and alternately warmed and cooled to keep the temperature between 40 and 50° C. This is followed by heating at 100° C. for 30 minutes more. The organic material is cooled and extracted with methylene chloride to give 16 g of 4-fluoro-2-nitrotoluene.

Workup

  1. temperaturealternately warmed
  2. temperaturecooled
  3. customthe temperature between 40 and 50° C
  4. temperatureThe organic material is cooled
  5. extractionextracted with methylene chloride

Sources & evidence

ORD record
ord-2ee120e614af43e9892804db6475cb6a
Source dataset
uspto-grants-2000_02
Patent number
US06020379

Linked notes

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