Benzene → 3-Bromobenzophenone

HRID 25855

Reaction equation

HRID 25855 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[Cl-].[Al+3].[Cl-].[Cl-].COCCOC.CCO.[CH:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:6])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 4

HCID 241Benzene2×HCID 74377Benzoyl chloride, 3-bromo-HCID 6451240Aluminum(III) ChlorideHCID 20074477Dimethoxyethane ethanol

Product 1

HCID 705483-BromobenzophenoneYield 92.4%

Procedure

1.65 ml (12.50 mmol) 3-Bromobenzoyl chloride was dissolved in 10 ml of dry benzene. This solution was then added cautiously under stirring to a suspension of 2.00 g (15.00 mmol, 1.20 eq.) aluminum chloride in 20 ml dry benzene at 10° C. After the complete addition the resulting mixture was refluxed for 5 h. After quenching the mixture by adding water and conc. hydrochloric acid the aq. layer was extracted with ethyl acetate. The comb. org. fractions were dried over Na2SO4 and evaporated. Column chromatography (hexanes/ether (9+1)) yielded 3.02 g (11.55 mmol, 92.40%) (3-Bromo-phenyl)-phenyl-methanone as a white solid.

Workup

  1. additionThis solution was then added cautiously
  2. additionAfter the complete addition the resulting mixture
  3. temperaturewas refluxed for 5 h
  4. customAfter quenching the mixture
  5. additionby adding water and conc. hydrochloric acid the aq. layer
  6. extractionwas extracted with ethyl acetate
  7. dry with materialfractions were dried over Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-1eb64021580b4023907a7a60833e8b00
Source dataset
uspto-grants-2005_02
Patent number
US06858600B2

Linked notes

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