Boron tribromide → 2-(2,4-Dichlorophenyl)benzoxazol-5-ol

HRID 1245365Notes

Reaction equation

HRID 1245365 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][C:12]=2[N:13]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 219116842-(2,4-Dichlorophenyl)-5-methoxybenzoxazole

Product 1

HCID 219117282-(2,4-Dichlorophenyl)benzoxazol-5-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(2,4-dichlorophenyl)-5-methoxybenzoxazole (0.5 g, 1.7 mmol) was dissolved in 25 mL dichloromethane. To the solution was added boron tribromide (8 mmol) and the mixture was allowed to stir at room temperature for 48 hours. The mixture was then diluted with 25 mL dichloromethane and washed sequentially with saturated sodium bicarbonate (2×25 mL), followed by brine. The organic layer was separated, dried over MgSO4 and filtered. The solvent was removed under reduced pressure, to provide 2-(2,4-dichlorophenyl)benzoxazol-5-ol, which was purified using flash chromatography.

Workup

  1. washwashed sequentially with saturated sodium bicarbonate (2×25 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-df525709af4e439e997e9f343e88b270
Source dataset
uspto-grants-2006_10
Patent number
US07125876B2

Reaction notes

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