3-Chlorobiphenyl → 1-Bromo-2-(3'-chlorobiphenyl-4-yl)ethanone

HRID 2120781

Reaction equation

HRID 2120781 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.Br[CH2:15][C:16]([Br:18])=[O:17].[Cl-].[Cl-].[Cl-].[Al+3]>C(Cl)Cl>[Br:18][C:16](=[O:17])[CH2:15][C:11]1[CH:10]=[CH:9][C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 163223-ChlorobiphenylHCID 61147Bromoacetyl bromideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 223354751-Bromo-2-(3'-chlorobiphenyl-4-yl)ethanoneYield 55.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

A mixture of 5 g (0.026 mole) of 3-chlorobiphenyl, 50 ml of methylene chloride, 6.95 g (0.034 mole) of bromoacetyl bromide is cooled to 0-5° C. and 4 g (0.030 mole) of aluminium trichloride are added thereto. Stirring is effected for 1 hour at 5° C. and then 4 hours at room temperature. The mixture is poured into a water/ice mixture, extracted with methylene chloride, the organic phase is washed with a 1 N HCl solution, drying is effected over sodium sulphate and the residue is evaporated under reduced pressure. 4.5 g of the title compound are obtained. M.p. 63-65° C.

Workup

  1. custom4 hours
  2. customat room temperature
  3. extractionextracted with methylene chloride
  4. washthe organic phase is washed with a 1 N HCl solution
  5. customdrying
  6. customthe residue is evaporated under reduced pressure

Sources & evidence

ORD record
ord-1bcff879b6fe41fd80ee4c1c7b3d2774
Source dataset
uspto-grants-2004_02
Patent number
US06693118B2

Linked notes

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