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

HRID 129104Notes

Reaction equation

HRID 129104 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>CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)(Cl)(Cl)Cl>[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 106.5%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

4,5-Dimethyl-1,3-dioxolene-2-one (11.4 g) was mixed with N-bromosuccinimide (19.6 g) and 2,2-azobis(2-methylpropionitrile) (0.5 g) in freshly distilled carbon tetrachloride (350 mL) and refluxed for 6 hours under an argon atmosphere. The reaction mixture was cooled in an ice bath after reflux and the precipitate formed was filtered off. The tiltrate was washed with water and brine, and dried over sodium sulfate. The solvent was evaporated to yield a yellow oil (20.54 g) which was distilled to obtain the pure monobromomethyl compound as a light yellow oil (11.86 g, 54%), bp 93° C. at 0.45 mm; 1H NMR (CDCl3) δ2.15 (s, 3H), 4.21 (S, 2H); IR (film) 1820, 1728, 1392, 1201, 1236, 768 cm-1.

Workup

  1. temperaturerefluxed for 6 hours under an argon atmosphere
  2. temperatureThe reaction mixture was cooled in an ice bath
  3. temperatureafter reflux
  4. customthe precipitate formed
  5. filtrationwas filtered off
  6. washThe tiltrate was washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-4e258e8f736a4bab90aa3e8e827714b5
Source dataset
uspto-grants-1995_11
Patent number
US05466811

Reaction notes

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