Boron tribromide → HCID 135794312, compound

HRID 2085197Notes

Reaction equation

HRID 2085197 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([C:11]2[O:15][C:14]3[CH:16]=[CH:17][CH:18]=[C:19]([O:20]C)[C:13]=3[CH:12]=2)=[N:8][N:7]=1)=[O:5])[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([C:11]2[O:15][C:14]3[CH:16]=[CH:17][CH:18]=[C:19]([OH:20])[C:13]=3[CH:12]=2)=[N:8][N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22729122HCID 22729122, compound

Product 1

HCID 135794312HCID 135794312, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Ethoxycarbonyl-2-(4-methoxybenzo(b)furan-2-yl)-1,3,4-oxadiazole (5.0 g) was dissolved in dichloromethane (40 ml) and boron tribromide (4.0 ml) was added dropwise with stirring under ice-cooling. Then, the mixture was stirred at room temperature for 5 hr, and the reaction mixture was poured into ice water. The mixture was stirred at it was at room temperature for 1 hr. The crystals were collected by filtration and dissolved in chloroform. The solution was washed with saturated aqueous solution of sodium hydrogencarbonate, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (2.5 g) as yellow crystals.

Workup

  1. temperaturecooling
  2. stirringThen, the mixture was stirred at room temperature for 5 hr
  3. stirringThe mixture was stirred at it
  4. filtrationThe crystals were collected by filtration
  5. dissolutiondissolved in chloroform
  6. washThe solution was washed with saturated aqueous solution of sodium hydrogencarbonate
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7cf81ad0a17c4caf9e00cbc7843cac33
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

Loading…