p-Nitroacetophenone → 2-Bromo-4'-nitroacetophenone

HRID 1085256Notes

Reaction equation

HRID 1085256 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)=[O:3].[Br:13]Br>C(Cl)(Cl)Cl>[N+:10]([C:7]1[CH:6]=[CH:5][C:4]([C:2](=[O:3])[CH2:1][Br:13])=[CH:9][CH:8]=1)([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 7487p-NitroacetophenoneHCID 24408Bromine

Product 1

HCID 668402-Bromo-4'-nitroacetophenoneYield 65.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

In 200 ml of chloroform was dissolved 8.25 g of 4-nitroacetophenone, and 20 ml of a chloroform solution containing 8 g of bromine was added dropwise thereto under cooling. The resulting reaction mixture was concentrated, and the residue (concentrate) was recrystallized from chloroform/ether, collected by filtration, washed, and dried to obtain 8.03 g of p-nitrophenacyl bromide.

Workup

  1. additionwas added dropwise
  2. temperatureunder cooling
  3. customThe resulting reaction mixture
  4. concentrationwas concentrated
  5. concentrationthe residue (concentrate)
  6. customwas recrystallized from chloroform/ether
  7. filtrationcollected by filtration
  8. washwashed
  9. customdried

Sources & evidence

ORD record
ord-125fa525a5a84c28a038d39d17b87b45
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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