Boron tribromide → 3-[4-(2-Chloro-ethoxy)-phenyl]-7-hydroxy-2-(4-hydroxy-phenyl)-3H-quinazolin-4-one

HRID 617125Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][C:16]([O:22]C)=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:24]2[CH:29]=[CH:28][C:27]([O:30]C)=[CH:26][CH:25]=2)=[CH:7][CH:6]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][C:16]([OH:22])=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: -30 °C

Procedure

To a chilled (-30° C.) solution of 1.0 g (0.00229 mol) of 3-[4-(2-chloro-ethoxy)-phenyl]-7-methoxy-2-(4-methoxy-phenyl)-3H-quinazolin-4-one in 300 mL of dry methylene chloride was added 23 mL (0.0229 mol) of boron tribromide (1M solution in dichloromethane (Aldrich Chemicals)). The reaction mixture was stirred at -30° C. for 20 minutes, under nitrogen, and then at room temperature overnight. The crude reaction mixture was added to 700 mL of aqueous sodium bicarbonate. The solution was stirred vigorously for 40 minutes at room temperature. The precipitate which formed was collected by vacuum filtration. The crude product when subjected to HPLC gave pure product. (mp 285-287° C.)

Workup

customat room temperature
customovernight
customThe crude reaction mixture
stirringThe solution was stirred vigorously for 40 minutes at room temperature
customThe precipitate which formed
filtrationwas collected by vacuum filtration
customgave pure product

Sources & evidence

ORD record: ord-a6fb99f46964464cbe7b93330c62e226
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05948775

Reaction notes

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