Benzene → 1-(4-Bromophenyl)-2-phenylethanone

HRID 1739354Notes

Reaction equation

HRID 1739354 reaction equation
[CH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[Br:11][C:12]1[CH:17]=[CH:16][C:15](CC(Cl)=O)=[CH:14][CH:13]=1.Cl.C([O:26][CH2:27][CH3:28])(=O)C>>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([C:27]([CH2:28][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:26])=[CH:16][CH:17]=1

Participants

6

Reactant 5

HCID 241Benzene2×HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 181552Benzeneacetyl chloride, 4-bromo-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 5197381-(4-Bromophenyl)-2-phenylethanoneYield 84%

Procedure

Benzene (200 mL) and aluminum chloride (74 g, 0.558 mol) are mixed into a flask and the mixture of 4-bromophenylacetyl chloride and benzene in Step (a) is added dropwise allowing the reaction to evolve HCl. The reaction mixture is stirred at room temperature for 1 to 1.5 hours and poured into ice water. Ethyl acetate (1 L) is added to dissolve the precipitated solids. The layers are separated and the organic layer is washed successively with 1 M aqueous HCl, saturated aqueous NaHCO3, brine and then dried over Na2SO2. The solvent is then evaporated to give a solid material which is recrystallized from ethylacetate/hexanes to give the title compound in 84% yield as a yellow solid.

Workup

  1. additionis added dropwise
  2. customthe reaction
  3. dissolutionto dissolve the precipitated solids
  4. customThe layers are separated
  5. washthe organic layer is washed successively with 1 M aqueous HCl, saturated aqueous NaHCO3, brine
  6. dry with materialdried over Na2SO2
  7. customThe solvent is then evaporated
  8. customto give a solid material which
  9. customis recrystallized from ethylacetate/hexanes

Sources & evidence

ORD record
ord-af5b1ba32e1843118c63e371c9166d9c
Source dataset
uspto-grants-1999_10
Patent number
US05965679

Reaction notes

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