Boron tribromide → HCID 135822829, compound

HRID 617132Notes

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](=[C:15]([O:22]C)[CH:16]=[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](=[C:15]([OH:22])[CH:16]=[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: 0 °C

Procedure

To a chilled (0° C.) solution of 3.5 g (0.00801 mol) of 3-[4-(2-chloro-ethoxy)-phenyl]-8-methoxy-2-(4-methoxy-phenyl)-3H-quinazolin-4-one in 100 mL of dry methylene chloride was added 35 mL (0.0352 mol) of boron tribromide (1M solution in dichloroethane (Aldrich Chemicals)). The reaction mixture was stirred at 0° C. for 20 minutes, under nitrogen, and then at room temperature overnight. The crude reaction mixture was added to 400 mL of aqueous sodium bicarbonate. The solution was stirred vigorously for 1 hour at room temperature. The precipitate which formed was collected by vacuum filtration. An analytical sample (mp 274-276° C.) was obtained by recrystallization from methanol.

Workup

customat room temperature
customovernight
customThe crude reaction mixture
stirringThe solution was stirred vigorously for 1 hour at room temperature
customThe precipitate which formed
filtrationwas collected by vacuum filtration
customAn analytical sample (mp 274-276° C.) was obtained by recrystallization from methanol

Sources & evidence

ORD record: ord-cd5d31b585024a97bbe5a0fdbb6cb18a
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05948775

Reaction notes

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