Cyclododecanone → 2-bromocyclododecanone

HRID 2198817Notes

Reaction equation

HRID 2198817 reaction equation
[Br:1]Br.[C:3]1(=[O:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>C(Cl)Cl>[CH2:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([Br:1])[C:3](=[O:15])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 13246CyclododecanoneHCID 24408Bromine

Product 1

HCID 357602-bromocyclododecanoneYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An amount of 183.8 gm (1.15 mol) of bromine was added dropwise with refluxing under a nitrogen atmosphere to a well agitated solution comprising 182.3 gm (1 mol) of cyclododecanone in 275 ml of methylene chloride over a period of six hours. Agitation was continued for 15 minutes and approximately one-half of the solvent was distilled off. The solution obtained by this method contained approximately 235 gm of α-bromocyclododecanone (90% yield) and was further reacted directly.

Workup

  1. temperaturewith refluxing under a nitrogen atmosphere to a well agitated solution
  2. customof six hours
  3. distillationapproximately one-half of the solvent was distilled off
  4. customThe solution obtained by this method

Sources & evidence

ORD record
ord-f329c1a06d6f4685bec4b23169a591ea
Source dataset
uspto-grants-1982_11
Patent number
US04360468

Reaction notes

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