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

HRID 1773215노트

반응식

HRID 1773215 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 1184524986-(Bromomethyl)benzofuran-2-carbonitrile

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ff9de797bd5a41e88f8992f9fb9a7a56
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255093B2

반응 노트

불러오는 중…