Azobisisobutyronitrile → 1,1'-Biphenyl, 4'-(bromomethyl)-2-nitro-

HRID 466705

反応式

HRID 466705 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 104431944'-Methyl-2-nitro-1,1'-biphenyl

生成物 1

HCID 117790721,1'-Biphenyl, 4'-(bromomethyl)-2-nitro-収率 37.2%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

A 2 L 24/40 three necked round-bottom flask equipped with a mechanical stirrer, a reflux condenser and a stopper, was charged with 15.427 g (72 mmol) of 4-methyl-2'-nitro[1,1'-biphenyl], 1.2 L of carbon tetrachloride, 14.164 g (80 mmol) of N-bromosuccinimide, and 0.50 g of 2,2'-azobis(2-methylpropionitrile). The stirred reaction mixture was refluxed under a nitrogen atmosphere for 4 hours, then cooled to room temperature and filtered. The filtrate was evaporated in vacuo and the residual oil was purified on a silica gel flash chromatography column eluted with 10% ethyl acetate-hexane. Evaporation of the pure fractions afforded the product as a yellow crystalline solid (7.83 g, 37%) which had: mp 109°-110° C.

後処理

  1. customThe stirred reaction mixture
  2. temperaturewas refluxed under a nitrogen atmosphere for 4 hours
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuo
  5. customthe residual oil was purified on a silica gel flash chromatography column
  6. washeluted with 10% ethyl acetate-hexane
  7. customEvaporation of the pure fractions

出典と根拠

ORDレコード
ord-b150302fcaab410589c6e234d12a84ae
出典データセット
uspto-grants-1992_10
特許番号
US05157026

関連ノート

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