N-bromobutanimide → 2-(Bromomethyl)thiophene-3-carbonitrile

HRID 1251178ノート

反応式

HRID 1251178 の反応式
[CH3:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]#[N:8].[Br:9]N1C(=O)CCC1=O>C1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:9][CH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]#[N:8]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 125657872-Methylthiophene-3-carbonitrile

生成物 1

HCID 225036202-(Bromomethyl)thiophene-3-carbonitrile収率 82%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 241Benzene溶媒

反応条件

温度
80 °C

実験手順

2-Methyl-3-cyanothiophene (2.108 g) was dissolved in benzene (30 ml), followed by the addition of N-bromosuccinimide (4.8 g) and 70% benzoyl peroxide (202 mg), and the mixture was stirred at 80° C. for 2 hr. The reaction mixture was cooled, and the resulting precipitates were filtered off. Then the filtrate was diluted with ethyl acetate, washed with an aqueous solution of saturated sodium bicarbonate, dried (over MgSO4) and then evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a yellow oil (2.746 g, yield; 82%).

後処理

  1. temperatureThe reaction mixture was cooled
  2. customthe resulting precipitates
  3. filtrationwere filtered off
  4. additionThen the filtrate was diluted with ethyl acetate
  5. washwashed with an aqueous solution of saturated sodium bicarbonate
  6. dry with materialdried (over MgSO4)
  7. customevaporated
  8. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

出典と根拠

ORDレコード
ord-79adb296255f4eb89e315f2b1e037f1a
出典データセット
uspto-grants-2002_01
特許番号
US06340759B1

反応ノート

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