4'-Fluoroacetophenone → 4'-Fluoro-3'-nitroacetophenone

HRID 581892Notes

Reaction equation

HRID 581892 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1)=[O:3].[N+:11]([O-])([O-:13])=[O:12].[K+]>S(=O)(=O)(O)O>[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 98284'-FluoroacetophenoneHCID 24434Potassium Nitrate

Product 1

HCID 27346124'-Fluoro-3'-nitroacetophenone

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
2.5 °C

Procedure

Concentrated sulfuric acid (200 ml) is cooled to 5° C. 4-Fluoroacetophenone (20 ml, 0.16 mol) is added keeping the temperature below 10° C. The mixture is cooled to 0-5° C. and potassium nitrate (25 g, 0.25 mol) is added portionwise over 2 hours keeping the temperature within this range. Following the addition the mixture is stirred in the cold for additionally 2 hours. The mixture is poured on ice (600 g) and the crude product is filtered off. Column-chromatographic purification on silica gel using a mixture of ethyl acetate and petroleum ether (1:9) as the eluent affords pure 1 g (18.2 g, 60%). Mp 48-49° C.

Workup

  1. customthe temperature below 10° C
  2. additionthe addition the mixture
  3. additionThe mixture is poured on ice (600 g)
  4. filtrationthe crude product is filtered off
  5. customColumn-chromatographic purification on silica gel using
  6. additiona mixture of ethyl acetate and petroleum ether (1:9) as the eluent
  7. customaffords pure 1 g (18.2 g, 60%)

Sources & evidence

ORD record
ord-8e2f7f41029e4dfaa41266732c552f75
Source dataset
uspto-grants-1999_07
Patent number
US05922725

Reaction notes

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