2-Methylcyclohexanone → 2-Bromo-2-methylcyclohexanone

HRID 619401

Reaction equation

HRID 619401 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 δ 3.21 (td, J=16 Hz, 8 Hz, 1 H, CH--CO), 2.36 (m, 2 H), 2.06 (m, 2 H), 1.82 (s, 3 H, Me), 1.77 (m, 2 H), 1.62 (m, 1 H).

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-81717842061e4df6984918f81742d7df
Source dataset
uspto-grants-1999_09
Patent number
US05958970

Linked notes

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