N-bromobutanimide → 4-(Bromomethyl)-5-methyl-1,3-dioxol-2-one

HRID 1601452Notes

Reaction equation

HRID 1601452 reaction equation
[CH3:1][C:2]1[O:3][C:4](=[O:8])[O:5][C:6]=1[CH3:7].[Br:9]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:9][CH2:1][C:2]1[O:3][C:4](=[O:8])[O:5][C:6]=1[CH3:7]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1422104,5-Dimethyl-1,3-dioxol-2-one

Product 1

HCID 107741414-(Bromomethyl)-5-methyl-1,3-dioxol-2-oneYield 112.3%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Combine 4,5-dimethyl-1,3-dioxol-2-one (3.42 g, 30 mmol), N-bromosuccinimide (5.34 g, 30 mmol) and AIBN (500 mg, 3 mmol) in anhydrous carbon tetrachloride (100 mL). Heat at reflux. After 2 hours, cool and filter. Concentrate the filtrate to give 4-bromomethyl-5-methyl-1,3-dioxol-2-one (6.5 g, crude) as an oil, which can be used for the next step without further purification.

Workup

  1. temperatureHeat
  2. temperatureat reflux
  3. temperaturecool
  4. filtrationfilter
  5. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-4a4501c9981543c0ae844cfdfd3cfbf1
Source dataset
uspto-grants-1999_11
Patent number
US05977139

Reaction notes

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