Bromine → 2-Bromo-4-chloro-1-(4-chlorophenyl)butan-1-one

HRID 1534667Notes

Reaction equation

HRID 1534667 reaction equation
[Br:1]Br.[Cl:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:8]>C(Cl)Cl>[Br:1][CH:6]([C:7]([C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1)=[O:8])[CH2:5][CH2:4][Cl:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 27237814,4'-Dichlorobutyrophenone

Product 1

HCID 1071672-Bromo-4-chloro-1-(4-chlorophenyl)butan-1-oneYield 88.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
10 °C

Procedure

A solution of 358 g of bromine in 350 ml of methylene chloride is added dropwise to a solution of 483 g (2.23 mols) of 4-chlorophenyl 3-chloropropyl ketone in 1200 ml of methylene chloride at 20° C. Stirring is continued for one hour and the mixture is then evaporated down in vacuo. 300 ml of petroleum ether are added to the residue, and stirring is continued until crystallization is complete. The mixture is cooled to 10° C., and the precipitate is filtered off under suction. 582 g (88.3% of theory) of 4-chlorophenyl 1-bromo-3-chloropropyl ketone of melting point 73° C. are obtained.

Workup

  1. customthe mixture is then evaporated down in vacuo
  2. addition300 ml of petroleum ether are added to the residue
  3. stirringstirring
  4. customis continued until crystallization
  5. filtrationthe precipitate is filtered off under suction

Sources & evidence

ORD record
ord-b6d6a2e154604cffb7a820bc03bdee58
Source dataset
uspto-grants-1992_02
Patent number
US05089640

Reaction notes

Loading…