Boron tribromide → 2-(7-hydroxyquinolin-4-yloxy)acetic Acid Hydrobromide

HRID 40318Notes

Reaction equation

HRID 40318 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.B(Br)(Br)[Br:19]>ClCCCl.C(Cl)Cl>[BrH:19].[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 576910212-(7-Methoxyquinolin-4-yloxy)acetic acid

Product 1

HCID 1363301242-(7-hydroxyquinolin-4-yloxy)acetic Acid HydrobromideYield 139.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a pressure vial was added 2-(7-methoxyquinolin-4-yloxy)acetic acid (1.00 g, 4.29 mmol) in DCE (0.6 M, 7 mL). The vial was cooled in an ice bath and to the solution was added BBr3 (1.62 ml, 17.2 mmol). The reaction was allowed to warm to room temperature and stirred overnight. While some starting material remained, the reaction was stopped and diluted with DCM (keep in hood due to fuming). The solids were filtered and dried over high vacuum to yield a light brown crude solid (˜1.8 g). The material was used without further purification.

Workup

  1. temperatureThe vial was cooled in an ice bath and to the solution
  2. filtrationThe solids were filtered
  3. customdried over high vacuum

Sources & evidence

ORD record
ord-081dcb9370e14bcaacbd6affeb9dbe26
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Reaction notes

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