1,2-Dichloroethane → 1-(4'-Bromo(1,1'-biphenyl)-4-yl)ethan-1-one

HRID 251770Notes

Reaction equation

HRID 251770 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].ClCCCl.[C:9](Cl)(=[O:11])[CH3:10].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:16][CH:15]=1>O>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:9](=[O:11])[CH3:10])=[CH:22][CH:21]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 111,2-Dichloroethane2×HCID 6367Acetyl chlorideHCID 71014-BromobiphenylHCID 6451240Aluminum(III) Chloride

Product 1

HCID 798061-(4'-Bromo(1,1'-biphenyl)-4-yl)ethan-1-oneYield 102.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Four point three grams (32 mmol) of aluminum chloride was placed into 30 milliliter of 1,2-dichloroethane and a solution made by dissolving 2.0 g (25 mmol) of acetyl chloride, subsequently 5.0 g (21 mmol) of 4-bromo biphenyl into 20 milliliter of 1,2-dichloroethane was added while cooling with ice. The mixed solution was stirred as it is while cooling with ice for 4 hours. After completion of the reaction, adding water and an extraction was carried out using dichloro-methane. Further, washing with water, dried with the use of sodium sulfate. Removing the solvent by distillation, 5.9 g of crude 1-(4′-bromo-biphenyl-4-yl)-ethanone was obtained.

Workup

  1. additionwas added
  2. temperaturewhile cooling with ice
  3. temperaturewhile cooling with ice for 4 hours
  4. customAfter completion of the reaction
  5. extractionan extraction
  6. washFurther, washing with water
  7. dry with materialdried with the use of sodium sulfate
  8. customRemoving the solvent
  9. distillationby distillation

Sources & evidence

ORD record
ord-77e2e9fe06a04dd18e6c45b442fccbf2
Source dataset
uspto-grants-2011_01
Patent number
US07867629B2

Reaction notes

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