Boron tribromide → HCID 3625866, compound

HRID 1245362Notes

Reaction equation

HRID 1245362 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:11]=3[N:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21911878HCID 21911878, compound

Product 1

HCID 3625866HCID 3625866, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(4-fluorophenyl)-5-methoxybenzoxazole (2.89 g, 11.89 mmol) in methylene chloride (70 mL) was added BBr3 (1 M in CH2Cl2, 13.08 mL) dropwise in an ice-bath. The resulting mixture was stirred at room temperature for 36 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in ethyl acetate (150 mL). The organic layer was washed sequentially with saturated sodium bicarbonate and brine, dried over sodium sulfate, and evaporated under reduced pressure. Column chromatography (ethyl acetate: Hexanes=1:4) gave 2-(4-fluorophenyl)benzoxazol-5-ol as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (150 mL)
  3. washThe organic layer was washed sequentially with saturated sodium bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-80153ee652d54ef5858c1e8b30620291
Source dataset
uspto-grants-2006_10
Patent number
US07125876B2

Reaction notes

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