1,3-Dibromo-5,5-dimethylhydantoin → 6-(Bromomethyl)-2,3-dihydro-4H-chromen-4-one

HRID 1042752노트

반응식

HRID 1042752 반응식
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2=[O:12].CC1(C)N([Br:19])C(=O)N(Br)C1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClC1C=CC=CC=1>[Br:19][CH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2=[O:12]

참가 물질

5

반응물 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 6547AzobisisobutyronitrileHCID 5843546-Methyl-4-chromanone

생성물 1

HCID 190195106-(Bromomethyl)-2,3-dihydro-4H-chromen-4-one수율 119.8%

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

실험 절차

A solution of 6-Methyl-2,3-dihydro-4H-chromen-4-one (7.2 g, 44 mmol), 5,5-Dimethyl-1,3-dibromohydantoin (7.7 g, 27 mmol), and Azobisisobutyronitrile (1.5 g, 9 mmol) in monochlorobenzene (140 mL) was stirred at 80° C. for 3 hours. The reaction solution was poured into ice water (100 mL), and the mixture was warmed to room temperature and then separated into aqueous and organic layers. The aqueous layer was extracted with dichloromethane (50 mL×2). The combined organic layers were washed with brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. The obtained concentrated residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain the title compound (7.8 g, 73%).

후처리

  1. customseparated into aqueous and organic layers
  2. extractionThe aqueous layer was extracted with dichloromethane (50 mL×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was then distilled off under reduced pressure
  6. customThe obtained concentrated residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-ff9d273a193a442e957c8809c611d7b6
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557998B2

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