Boron tribromide → 5,7-dihydroxy-3-(4-hydroxyphenyl)-4(3H)-quinazolinone

HRID 130332Notes

Reaction equation

HRID 130332 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]([O:13]C)[CH:10]=[C:9]2[C:4]=1[C:5](=[O:23])[N:6]([C:15]1[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=1)[CH:7]=[N:8]2.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:12]=[C:11]([OH:13])[CH:10]=[C:9]2[C:4]=1[C:5](=[O:23])[N:6]([C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1)[CH:7]=[N:8]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 116881915,7-Dimethoxy-3-(4-methoxyphenyl)quinazoline-4-one

Product 1

HCID 104232345,7-dihydroxy-3-(4-hydroxyphenyl)-4(3H)-quinazolinoneYield 52.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled mixture of 365 mg (1.17 mmol) of 5,7-dimethoxy-3-(4-methoxyphenyl)-4(3H)-quinazolinone, prepared according to the procedures described in Example 18 or 19, and 10 ml of CH2Cl2, 3 ml of BBr3 (31.7 mmol) was added. The mixture was stirred at room temperature for 2 days. The solvent was evaporated, the obtained residue treated with a cold NaHCO3 solution and extracted with EtOAc. The organic layer was washed with water and brine, dried over MgSO4 and evaporated to yield a solid which purification by flash chromatography on silica gel (loaded with CH2Cl2 and eluted with 66% EtOAc in hexane) gave 165 mg of 5,7-dihydroxy-3-(4-hydroxyphenyl)-4(3H)-quinazolinone (40% yield) as a white solid.

Workup

  1. customprepared
  2. additionwas added
  3. customThe solvent was evaporated
  4. additionthe obtained residue treated with a cold NaHCO3 solution
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. customto yield
  10. customa solid which purification by flash chromatography on silica gel (loaded with CH2Cl2 and eluted with 66% EtOAc in hexane)

Sources & evidence

ORD record
ord-9d360a339fdc472ab1f77b30ad46268c
Source dataset
uspto-grants-2008_06
Patent number
US07381730B2

Reaction notes

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