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

HRID 1773215Notes

Reaction equation

HRID 1773215 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 1184524986-(Bromomethyl)benzofuran-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ff9de797bd5a41e88f8992f9fb9a7a56
Source dataset
uspto-grants-2016_02
Patent number
US09255093B2

Reaction notes

Loading…