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

HRID 1024422Notes

Reaction equation

HRID 1024422 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].[Cl-].[Al+3].[Cl-].[Cl-].[Br:17]Br>CCOCC>[Br:17][CH2:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=1)=[O:3]

Participants

5

Reactant 3

HCID 7487p-NitroacetophenoneHCID 24408BromineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 668402-Bromo-4'-nitroacetophenoneYield 69%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Nitroacetophenone (25 g) in ether (250 ml) was treated with aluminium chloride (catalytic amount) followed by bromine (7.77 ml) for 10 minutes and the reaction was stirred for 30 minutes. The reaction was quenched with aqueous NaHCO3, the ether layer was separated, dried using Na2SO4 and concentrated. The residue was dissolved in EtOAc, dried using Na2SO4, and concentrated to get off white solid which was crystallized in EtOAc/Pet ether to yield 25.5 gm (69%) of the title compound. 1HNMR (CDCl3, 300 MHz): δ 8.19 (d, 2H), 8.36 (d, 2H), 4.47 (s, 2H).

Workup

  1. customThe reaction was quenched with aqueous NaHCO3
  2. customthe ether layer was separated
  3. customdried
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in EtOAc
  6. customdried
  7. concentrationconcentrated
  8. customto get off white solid which
  9. customwas crystallized in EtOAc/Pet ether

Sources & evidence

ORD record
ord-7307ac3dbf3840e1aa8cc80107f317fb
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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