Isophorone → 4-Bromo-3,5,5-trimethylcyclohex-2-en-1-one

HRID 1287174Notes

Reaction equation

HRID 1287174 reaction equation
[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([CH3:10])=[CH:3]1.[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[CH3:10][C:4]1[CH:5]([Br:11])[C:6]([CH3:8])([CH3:7])[CH2:9][C:2](=[O:1])[CH:3]=1

Participants

5

Reactant 3

HCID 6544IsophoroneHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimide

Product 1

HCID 127940644-Bromo-3,5,5-trimethylcyclohex-2-en-1-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of isophorone (13.82 g; 0.1 Mole) and N-bromo-succinimide (17.80 g; 0.1 Mole) in the presence of traces of α, α'-azodiisobutyronitrile was refluxed in 500 ml of CCl4 during 15 minutes. 500 ml of petrol-ether (30°-50°C) were then added to the cool reaction mixture and the succinimide thus precipitated was filtered off. By evaporating the volatile components of the clear filtrate, crude 3,5,5-trimethyl-4-bromo-cyclohex-2-en-1-one was obtained. NMR (CCl4): 1.16 (3H,s); 1.25 (3H,s); 2.11 (3H,s); 2.07 (1H,d, J=16 cps); 2.53 (1H,d, J=16 cps); 4.45 (1H,s); 5.78 (1H,s) δ ppm.

Workup

  1. customthe succinimide thus precipitated
  2. filtrationwas filtered off
  3. customBy evaporating the volatile components of the clear filtrate

Sources & evidence

ORD record
ord-623a7521f8a04d4d835a4ed823b35c9c
Source dataset
uspto-grants-1976_10
Patent number
US03983885

Reaction notes

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