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

HRID 1518100ノート

反応式

HRID 1518100 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-9bb4512e97c54a6998abbd61ed1dcf93
出典データセット
uspto-grants-2012_07
特許番号
US08232405B2

反応ノート

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