Bromine → 1,3-Cyclohexanedione, 2-bromo-5,5-dimethyl-

HRID 417915Notes

Reaction equation

HRID 417915 reaction equation
[Br:1]Br.[CH3:3][C:4]1([CH3:12])[CH2:9][C:8](=[O:10])[CH2:7][C:6](=[O:11])[CH2:5]1>CC(O)=O>[Br:1][CH:7]1[C:8](=[O:10])[CH2:9][C:4]([CH3:12])([CH3:3])[CH2:5][C:6]1=[O:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 31358Dimedone

Product 1

HCID 709581,3-Cyclohexanedione, 2-bromo-5,5-dimethyl-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (0.51 mL, 10 mmol) was added dropwise to a solution of 5,5-dimethylcyclohexane-1,3-dione (1.4 g, 10 mmol) in AcOH (20 mL) at r.t. The reaction mixture was stirred for 2 h and then the product was isolated by filtration. The precipitate was washed with Et2O (2×100 mL) and then dried in vacuo give the title compound in quantitative yield as a light brown solid, which was used without further purification. LCMS (ES+) 218.9 (M+H)+.

Workup

  1. customthe product was isolated by filtration
  2. washThe precipitate was washed with Et2O (2×100 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-e2ff66c0b47248f391cb50a657f3e762
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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