1,3-Cyclohexanedione → 2-Bromocyclohexane-1,3-dione

HRID 2383417Notes

Reaction equation

HRID 2383417 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=[O:7])[CH2:2]1.[Br:9]Br>ClCCl>[Br:9][CH:2]1[C:3](=[O:7])[CH2:4][CH2:5][CH2:6][C:1]1=[O:8]

Participants

4

Reactant 2

HCID 104341,3-CyclohexanedioneHCID 24408Bromine

Product 1

HCID 27704762-Bromocyclohexane-1,3-dioneYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1,3 Cyclohexandione (10 g, 89 mmol) in dichloromethane (22 mL) at 0° C. was added a solution of bromine (3.8 mL, 89 mmol) in dichloromethane (3 mL) over a period of 10 minutes. The reaction mixture was stirred at room temperature for 1.5 hours. The reaction mixture was filtered and the residue washed with hexane (200 mL). The residue was taken into water (75 mL) and heated at 80° C. for 30 minutes. It was cooled to room temperature, filtered and dried under reduced pressure to give the desired product (14 g, 82%) as a solid. ESMS [M+H]: 191.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe residue washed with hexane (200 mL)
  3. temperatureheated at 80° C. for 30 minutes
  4. temperatureIt was cooled to room temperature
  5. filtrationfiltered
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-77fd35eb05c743b7834e9c0122742e7f
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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