N-bromobutanimide → 6-(Bromomethyl)benzofuran-2-carbonitrile

HRID 1773215ノート

反応式

HRID 1773215 の反応式
[CH3:1][C:2]1[CH:12]=[CH:11][C:5]2[CH:6]=[C:7]([C:9]#[N:10])[O:8][C:4]=2[CH:3]=1.C1C(=O)N([Br:20])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:1][C:2]1[CH:12]=[CH:11][C:5]2[CH:6]=[C:7]([C:9]#[N:10])[O:8][C:4]=2[CH:3]=1

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 289100396-Methylbenzofuran-2-carbonitrile

生成物 1

HCID 1184524986-(Bromomethyl)benzofuran-2-carbonitrile

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

6-methylbenzofuran-2-carbonitrile (12 g, 76 mmol), NBS (13.59 g, 76 mmol), and AlBN (1.25 g, 7.64 mmol) were dissolved in carbon tetrachloride (191 ml). The mixture was heated to reflux overnight. After 18 h the reaction was cooled to RT and concentrated under reduced pressure. The product was then crashed out using MeOH and the slurry was placed in the fridge overnight. The slurry was filtered and the collected PPT was washed with MeOH. The collected PPT was pure 6-(bromomethyl)benzofuran-2-carbonitrile (13.864 g). 1H NMR (400 MHz, DMSO-d6) δ 4.87 (s, 2H), 7.52 (dd, J=8.2, 1.4 Hz, 1H), 7.83 (d, J=8.2 Hz, 1H), 7.87 (d, J=1.5 Hz, 1H), 8.11 (d, J=1.0 Hz, 1H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. customwas placed in the fridge overnight
  5. filtrationThe slurry was filtered
  6. washthe collected PPT was washed with MeOH

出典と根拠

ORDレコード
ord-ff9de797bd5a41e88f8992f9fb9a7a56
出典データセット
uspto-grants-2016_02
特許番号
US09255093B2

反応ノート

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