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Dichloromethane → 6-nitro-2,2-dimethyl-3-bromomethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran

HRID 1655377
ノート
印刷プレビュー

反応式

HRID 1655377 の反応式
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:15])=[C:9]([N:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]3=[O:22])[C:8]=2[CH:23]=1)([O-:3])=[O:2].[Br:24]N1C(=O)CCC1=O.ClCCl>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH2:15][Br:24])=[C:9]([N:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]3=[O:22])[C:8]=2[CH:23]=1)([O-:3])=[O:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 221228176-nitro-2,2,3-trimethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran

生成物 1

HCID 193872966-nitro-2,2-dimethyl-3-bromomethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran収率 73.2%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒
HCID 5943
Carbon Tetrachloride
溶媒

反応条件

温度
60 °C

実験手順

A suspension of 6-nitro-2,2,3-trimethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran (1.62 g, 0.0052 mol) in carbon tetrachloride (10 ml) containing benzoyl peroxide (20 mg) was heated to 60° C. N-bromosuccinimide (0.92 g, 0.0052 mol) was added and the mixture heated at reflux for seventeen hours. The cooled solution was treated with dichloromethane and aqueous ferrous sulfate solution, the organic phase was separated and evaporated under reduced pressure. The residue was chromatographed on silica gel, eluting with dichloromethane/acetone (92.5/7.5). The product was washed with diethyl ether/pentane to give 1.49 g of 6-nitro-2,2-dimethyl-3-bromomethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran, m.p. 221° C.

後処理

  1. temperaturethe mixture heated
  2. temperatureat reflux for seventeen hours
  3. customthe organic phase was separated
  4. customevaporated under reduced pressure
  5. customThe residue was chromatographed on silica gel
  6. washeluting with dichloromethane/acetone (92.5/7.5)
  7. washThe product was washed with diethyl ether/pentane

出典と根拠

ORDレコード
ord-4adc20fd40cb49dcb89479b23abac817
出典データセット
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05250547

反応ノート

読み込み中…

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