Nitric Acid → 5-Fluoro-2-nitrotoluene

HRID 614770Notes

Reaction equation

HRID 614770 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[N+:9]([O-])([OH:11])=[O:10]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[C:4]([CH3:8])[CH:3]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 9606m-Fluorotoluene

Product 1

HCID 949565-Fluoro-2-nitrotoluene

Procedure

A solution of 200 g of 3-fluorotoluene and 670 ml of concentrated nitric acid was heated at 50°-55° for 8 hours; after standing overnight, the reaction mixture was poured into 1200 ml of ice-water. The organic layer was separated, and the aqueous layer was extracted three times with ether; the organic fraction and the ethereal extracts were combined, washed once with water and saturated sodium chloride solution. The combined organic fraction was dried over magnesium sulfate, filtered, and evaporated under reduced pressure to give a yellow oil. This crude product was distilled using a 30-cm vacuum-jacketed column filled with glass helices to yield 192.7 g of 5-fluoro-2-nitrotoluene, bp 74.5°-77°/4 mm.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted three times with ether
  3. washwashed once with water and saturated sodium chloride solution
  4. dry with materialThe combined organic fraction was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto give a yellow oil
  8. distillationThis crude product was distilled
  9. additionfilled with glass helices

Sources & evidence

ORD record
ord-628e639e58554f62a7ca4c7f03a6d3b8
Source dataset
uspto-grants-1979_03
Patent number
US04146625

Reaction notes

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