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

HRID 129104노트

반응식

HRID 129104 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6547Azobisisobutyronitrile촉매HCID 5943Carbon Tetrachloride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4e258e8f736a4bab90aa3e8e827714b5
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466811

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