Boron tribromide → HCID 3625866, compound

HRID 2217176Notes

Reaction equation

HRID 2217176 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-d8d955f3713d4e1db5647829062d12ae
Source dataset
uspto-grants-2008_08
Patent number
US07407960B2

Reaction notes

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