N-bromobutanimide → 3-Bromo-4-chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran

HRID 440656노트

반응식

HRID 440656 반응식
[Cl:1][C:2]1[C:7]2[CH2:8][C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[C:5]([N+:13]([O-:15])=[O:14])=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:16][CH:8]1[C:7]2[C:2]([Cl:1])=[CH:3][CH:4]=[C:5]([N+:13]([O-:15])=[O:14])[C:6]=2[O:10][C:9]1([CH3:12])[CH3:11]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 224047764-Chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran

생성물 1

HCID 224048153-Bromo-4-chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran수율 95.4%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

A mixture of 11.82 g (0.052 mole) of 4-chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran (Example 1, Step C) and 9.3 g (0.052 mole) of N-bromosuccinimide in 200 mL of carbon tetrachloride was irradiated with a sun lamp for approximately 16 hours. No reaction occurred during this time. To this mixture was then added 0.10 g of benzoyl peroxide, and the reaction mixture was then heated at reflux and irradiated simultaneously for a period of five hours. The sun lamp was turned off, and the mixture was allowed to stir while being heated at reflux for an additional hour. The mixture was then passed through a column of silica gel, and product-containing fractions were combined. The solvent was evaporated from the combined fractions under reduced pressure, leaving 15.2 g of 3-bromo-4-chloro-2,3-dihydro-2,2-dimethyl-7-nitrobenzofuran as a solid, m.p. 103°-104° C.

후처리

  1. customwas irradiated with a sun lamp for approximately 16 hours
  2. temperaturethe reaction mixture was then heated
  3. temperatureat reflux
  4. customirradiated simultaneously for a period of five hours
  5. temperaturewhile being heated
  6. temperatureat reflux for an additional hour
  7. additionproduct-containing fractions
  8. customThe solvent was evaporated from the combined fractions under reduced pressure

출처 및 근거

ORD 기록
ord-e054de35a3e44bf4a04a6d695b45b00d
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521147

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