Boron tribromide → 2-Chloro-8-quinazolinol

HRID 2079607Notes

Reaction equation

HRID 2079607 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[C:5]([O:12]C)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 199886952-Chloro-8-methoxyquinazoline

Product 1

HCID 591992302-Chloro-8-quinazolinolYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0.55M solution of 2-chloro-8-methoxyquinazoline in DCM was added boron tribromide (2.2 eq. of a 1.0 M solution in DCM) over 5 minutes at 0° C. The reaction mixture was stirred at ambient temperature for 22 hours, and then cooled to −5° C. for 30 minutes. The precipitate was collected by vacuum filtration and then stirred in ice water for 30 minutes. The solid was collected by vacuum filtration and rinsed with 2-propanol. The off-white solid was dried in a desiccator to give the desired product in 79% yield. ES/MS m/z 181 (MH+).

Workup

  1. temperaturecooled to −5° C. for 30 minutes
  2. filtrationThe precipitate was collected by vacuum filtration
  3. stirringstirred in ice water for 30 minutes
  4. filtrationThe solid was collected by vacuum filtration
  5. washrinsed with 2-propanol
  6. customThe off-white solid was dried in a desiccator

Sources & evidence

ORD record
ord-78b622ebc6764d84b2c9c5a536d0be1f
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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