Bromine → 1-Bromo-4-chloro-3,3,6-trimethylhept-5-en-2-one

HRID 981797Notes

Reaction equation

HRID 981797 reaction equation
[CH3:1][C:2](=[CH:4][CH:5]([Cl:12])[C:6]([CH3:11])([CH3:10])[C:7](=[O:9])[CH3:8])[CH3:3].[Br:13]Br>C(Cl)(Cl)Cl.Cl>[CH3:3][C:2](=[CH:4][CH:5]([Cl:12])[C:6]([CH3:11])([CH3:10])[C:7](=[O:9])[CH2:8][Br:13])[CH3:1]

Participants

5

Reactant 2

HCID 24408BromineHCID 132983224-Chloro-3,3,6-trimethylhept-5-en-2-one

Product 1

HCID 200710531-Bromo-4-chloro-3,3,6-trimethylhept-5-en-2-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6212ChloroformSolvent

Procedure

6.03 g (0.032 mol) of 2,5,5-trimethyl-4-chloro-2-hepten-6-one are dissolved in 75 ml of chloroform, 2 drops of an ethereal hydrogen chloride solution are added, and 5.12 g (0.032 mol) of bromine are then added in one portion at 25° C. The mixture is stirred for 2.5 hours at room temperature, and hydrogen bromide and solvent are distilled off in vacuo; the final residues are removed in a high vacuum. 8.7 g are obtained of crude, 2,5,5-trimethyl-4-chloro-7-bromo-2-hepten-6-one, the structure of which is confirmed by the 1H-NMR spectrum. It is used directly in the next stage:

Workup

  1. distillationhydrogen bromide and solvent are distilled off in vacuo
  2. customthe final residues are removed in a high vacuum

Sources & evidence

ORD record
ord-1813d1790b8a4796a8c9a3d3d6daf630
Source dataset
uspto-grants-1991_02
Patent number
US04992577

Reaction notes

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