Methane → 2-Bromo-4'(-p-tolyl)acetophenone

HRID 485399Notes

Reaction equation

HRID 485399 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[Br:18][CH2:19][C:20](Br)=[O:21].C>CO.CC(C)=O.C(O)(=O)C.C(=S)=S>[Br:18][CH2:19][C:20]([C:11]1[CH:10]=[CH:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:13][CH:12]=1)=[O:21]

Participants

9

Reactant 4

HCID 297MethaneHCID 125664-MethylbiphenylHCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 135319782-Bromo-4'(-p-tolyl)acetophenone

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 887MethanolSolventHCID 6348Carbon DisulfideSolvent

Procedure

An 11.7 g. portion of 4-methylbiphenyl was dissolved in 75 ml. of carbon disulfide and cooled in an ice bath while 11.6 g. of aluminum chloride was added portionwise with vigorous stirring. A 15.9 g. portion of bromoacetylbromide was added dropwise and after completion and the reaction subsided the mixture was heated at reflux for 3 hours, then cooled overnight. The mixture was poured into crushed ice and 150 ml. of acetic acid and stirred for 1.5 hours. The resulting gum was collected and stirred in methanol for 2 hours, giving a solid. This solid was dissolved in methanol:acetone, treated with charcoal and cooled. The solution was decanted, concentrated to about 150 ml., decanted and recooled giving a solid which was collected, giving the desired intermediate as a beige solid, m.p. 120°-122° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperaturecooled overnight
  4. additionThe mixture was poured
  5. custominto crushed ice and 150 ml
  6. customThe resulting gum was collected
  7. customgiving a solid
  8. temperaturecooled
  9. customThe solution was decanted
  10. concentrationconcentrated to about 150 ml
  11. custom, decanted
  12. customrecooled giving a solid which
  13. customwas collected

Sources & evidence

ORD record
ord-99dfa56c9f034ce6bfea04b037919035
Source dataset
uspto-grants-1985_08
Patent number
US04536517

Reaction notes

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