Bromine → 2-Bromo-1-(2,3,4-trichlorophenyl)ethan-1-one

HRID 462421Notes

Reaction equation

HRID 462421 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].C([O-])(=O)C.[Na+].[Br:18]Br>CCCCCC>[Br:18][CH2:11][C:10]([C:3]1[CH:4]=[CH:5][C:6]([Cl:9])=[C:7]([Cl:8])[C:2]=1[Cl:1])=[O:12]

Participants

5

Reactant 3

HCID 24408BromineHCID 261322',3',4'-TrichloroacetophenoneHCID 517045Sodium Acetate

Product 1

HCID 30188652-Bromo-1-(2,3,4-trichlorophenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

A mixture of 2',3',4'-trichloroacetophenone (21.4 g, 0.0958 mole), anhydrous sodium acetate (8.0 g), and n-hexane (50 ml) was heated under reflux while treated with a solution of bromine (15.3 g, 0.096 mole) in 25 ml of n-hexane in five portions, decolorizing before each new addition. The mixture was then filtered while hot and the insoluble residue was triturated twice with 50 ml of boiling n-hexane. Enough additional n-hexane was added to the combined filtrates to avoid oiling out of product at 40°. The solution was then seeded and cooled at -10° for 18 hours. Product was collected and air dried to give 17.9 g (62%), mp 44°-46°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. additiondecolorizing before each new addition
  4. filtrationThe mixture was then filtered while hot and the insoluble residue
  5. customwas triturated twice with 50 ml of boiling n-hexane
  6. additionEnough additional n-hexane was added to the combined filtrates
  7. customto avoid oiling out of product at 40°
  8. temperaturecooled at -10° for 18 hours
  9. customProduct was collected
  10. customair dried
  11. customto give 17.9 g (62%), mp 44°-46°

Sources & evidence

ORD record
ord-9f2cb78a6acb4df3a0470217029c4b4d
Source dataset
uspto-grants-1985_05
Patent number
US04515793

Reaction notes

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