8-Methylquinoline → 8-(Bromomethyl)quinoline

HRID 327435

反応式

HRID 327435 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:12][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

参加物

5

反応物 2

HCID 119108-MethylquinolineHCID 67184N-bromobutanimide

生成物 1

HCID 3469148-(Bromomethyl)quinoline収率 54.9%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of 8-methylquinoline (45 g, 0.314 mol), N-bromosuccinimide (55 g, 0.309 mol) and benzoyl peroxide (1.5 g) in carbon tetrachloride (250 mL) was refluxed for 7 hours. The reaction was filtered and evaporated, and the crude product was crystallized from methanol (70 mL) to give 37.7 g of product. The mother liquors were chromatographed on silica gel in chloroform to give 17 g of material which was crystallized from ethyl acetate:hexane to give an additional 12.0 g of product.

後処理

  1. temperaturewas refluxed for 7 hours
  2. filtrationThe reaction was filtered
  3. customevaporated
  4. customthe crude product was crystallized from methanol (70 mL)

出典と根拠

ORDレコード
ord-b7ace455fc304e83b893bd03f7303095
出典データセット
uspto-grants-1993_12
特許番号
US05273975

関連ノート

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