m-Fluorotoluene → 5-Fluoro-2-nitrotoluene

HRID 376444

Reaction equation

HRID 376444 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[N+:9]([O-])([O-:11])=[O:10].[K+]>S(=O)(=O)(O)O>[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

4

Reactant 2

HCID 9606m-FluorotolueneHCID 24434Potassium Nitrate

Product 1

HCID 949565-Fluoro-2-nitrotoluene

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

3-Fluorotoluene (1 mole) in concentrated sulfuric acid (200 ml.) is stirred at 0° C. while a cold solution of potassium nitrate (1.5 mole) in concentrated sulfuric acid (750 ml.) is added slowly during 3 hours, the temperature being kept below 5° C. with an ice-ethanol bath After the addition is complete, the ice-bath is removed and stirring is continued for 3 hours at room temperature. Water (400 ml.) is added, and the organic layer is separated, dried (MgSO4) and filtered. The oil is separated by vapor-phase chromatograph on a 200×1 cm. silicone oil column (DC 200 20%) on Chromosorb R (60/80) at 191° C. and a helium flow rate of 86 ml./min. The desired pure nitro-isomer is collected.

Workup

  1. additionis added slowly during 3 hours
  2. customthe temperature being kept below 5° C. with an ice-ethanol bath
  3. additionAfter the addition
  4. customthe ice-bath is removed
  5. additionWater (400 ml.) is added
  6. customthe organic layer is separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customThe oil is separated by vapor-phase chromatograph on a 200×1 cm
  10. customat 191° C.
  11. customThe desired pure nitro-isomer is collected

Sources & evidence

ORD record
ord-e0580b885415450aac93fae5585ef695
Source dataset
uspto-grants-2000_02
Patent number
US06020379

Linked notes

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