2-Methylcyclohexanone → 2-Bromo-2-methylcyclohexanone

HRID 1934514Notes

Reaction equation

HRID 1934514 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8].[Br:9]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:9][C:2]1([CH3:1])[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8]

Participants

4

Reactant 2

HCID 114192-MethylcyclohexanoneHCID 67184N-bromobutanimide

Product 1

HCID 111168532-Bromo-2-methylcyclohexanoneYield 100%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 15 g (0.134 mol) of 2-methyl-1-cyclohexanone (7) and 23.84 g (0.134 mol) of N-bromosuccinimide in 150 mL of carbon tetrachloride was stirred and heated to reflux for 12 h under argon. The mixture was cooled to room temperature, filtered through Celite to remove succinimide and the filter cake was washed with 150 mL of ether. The filtrate was concentrated to give 25.6 g (100% yield) of 2-bromo-2-methyl-1-cyclohexanone. 1H NMR δ3.21 (td, J=16 Hz, 8 Hz, 1H, CH—CO), 2.36 (m, 2H), 2.06 (m, 2H), 1.82 (s, 3H, Me), 1.77 (m, 2H), 1.62 (m, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 12 h under argon
  3. filtrationfiltered through Celite
  4. customto remove succinimide
  5. washthe filter cake was washed with 150 mL of ether
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-36c43c07512f47b49a06e94b902f7d76
Source dataset
uspto-grants-2002_05
Patent number
US06384045B1

Reaction notes

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