Water → HCID 23026025, compound

HRID 1437483Notes

Reaction equation

HRID 1437483 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([O:15]C)[CH:10]=3)[O:8][C:4]=2[CH:3]=1.B(Br)(Br)Br.O>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=3)[O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 23025585HCID 23025585, compound

Product 1

HCID 23026025HCID 23026025, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 6-bromo-2-(3-methoxyphenyl)benzoxazole (Compound of Example 242) (19.45 g) in chloroform (800 ml) was added dropwise boron tribromide (100.05 g) at 0° C., and the mixture was stirred at room temperature for 4 hours and 65° C. for 9 hours. The reaction mixture was poured into water, and the mixture was stirred at room temperature for 30 minutes and extracted with chloroform-tetrahydrofuran (4:1, v/v). The organic layer was washed with water and dried over MgSO4, and the solvent was distilled off under reduced pressure. The resulting crystals were collected by filtration to obtain 3-(6-bromobenzoxazol-2-yl)phenol (16.46 g, 89%).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. extractionextracted with chloroform-tetrahydrofuran (4:1
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. distillationthe solvent was distilled off under reduced pressure
  6. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-c1c1b8cf154e4ef1a97245f52f98de0b
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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