Boron tribromide → HCID 135794312, compound

HRID 460625Notes

Reaction equation

HRID 460625 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-ccd3ef1ea9bf470380de25cfad8abd97
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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