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

HRID 129104ノート

反応式

HRID 129104 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 107741414-(Bromomethyl)-5-methyl-1,3-dioxol-2-one収率 106.5%

試薬・触媒・溶媒 2

HCID 6547Azobisisobutyronitrile触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4e258e8f736a4bab90aa3e8e827714b5
出典データセット
uspto-grants-1995_11
特許番号
US05466811

反応ノート

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