N-bromobutanimide → HCID 69442700, compound

HRID 446162Notes

Reaction equation

HRID 446162 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:16][C:17]1[CH:25]=[CH:24][C:20]2[CH:21]=[CH:22][S:23][C:19]=2[CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>ClCCCl>[Br:1][C:21]1[C:20]2[CH:24]=[CH:25][C:17]([O:16][CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:18][C:19]=2[S:23][CH:22]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 69443998HCID 69443998, compound

Product 1

HCID 69442700HCID 69442700, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

N-bromosuccinimide (15.70 g, 83.92 mmol) and p-toluenesulfonic add (2.70 g, 15.68 mmol) were added to a solution of 6-benzyloxy-benzothiophene (Zhengying C., CN 1370533 A, 21.2 g, 88.33 mmol) in 1,2-dichloroethane (120 ml). The mixture was maintained at 80° C. for 35 min, cooled in an ice bath, and the succinimide was removed by filtration. The solution was extracted with saturated sodium bicarbonate solution, dried over Na2SO4, filtered, and concentrated under vacuum to give an oil. Crystallisation from pentane afforded a white solid (21.60 g, 92%, mp: 68° C.).

Workup

  1. temperaturecooled in an ice bath
  2. customthe succinimide was removed by filtration
  3. extractionThe solution was extracted with saturated sodium bicarbonate solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto give an oil
  8. customCrystallisation from pentane

Sources & evidence

ORD record
ord-931974130eea4ddfb48e56bba16d2aa5
Source dataset
uspto-grants-2013_07
Patent number
US08476455B2

Reaction notes

Loading…