Cyclohexyl methyl ketone → 2-Bromo-1-cyclohexylethanone

HRID 2091053Notes

Reaction equation

HRID 2091053 reaction equation
[CH:1]1([C:7](=[O:9])[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:10]Br.S([O-])([O-])=O.[Na+].[Na+]>CO>[Br:10][CH2:8][C:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:9]

Participants

5

Reactant 3

HCID 13207Cyclohexyl methyl ketoneHCID 24408BromineHCID 24437Sodium Sulfite

Product 1

HCID 111600272-Bromo-1-cyclohexylethanoneYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution (50 mL) of 1-cyclohexylethanone (25.0 g) in methanol was added bromine (10.1 mL) at 0° C., and the mixture was stirred at room temperature for 30 min. Saturated sodium sulfite aqueous solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-10% ethyl acetate/hexane) to give the title object compound (25.8 g, 63%) as a colorless oil.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (0-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c444b721cc2841e3b4d8d7d224fab347
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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