Hydrogen Peroxide → 2-Bromo-6-methoxyquinolin-3-ol

HRID 2045717Notes

Reaction equation

HRID 2045717 reaction equation
[OH:1]O.[Br:3][C:4]1[C:13](B(O)O)=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:17][CH3:18])[CH:10]=2)[N:5]=1.[NH4+].[Cl-]>CCOCC.O>[Br:3][C:4]1[C:13]([OH:1])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:17][CH3:18])[CH:10]=2)[N:5]=1

Participants

6

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 25517Ammonium Chloride2×HCID 57416465(2-Bromo-6-methoxyquinolin-3-yl)boronic acid

Product 1

HCID 580913652-Bromo-6-methoxyquinolin-3-olYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Aqueous H2O2 (30%, 32.8 mL, 321 mmol) was added dropwise to a stirred solution of (2-bromo-6-methoxyquinolin-3-yl)boronic acid (4.64 g, 16.45 mmol) and NH4Cl (3.29 g, 61.5 mmol) in Et2O (82 mL) and water (82 mL). After 13 h, NH4Cl (3.29 g, 61.5 mmol) and aqueous H2O2 (30%, 32.8 mL, 321 mmol) were added, and the mixture was stirred for 48 h. The precipitate was collected and washed with water, then dried at 50° C. to afford the title compound (4.18 g, 100%) as a solid that was used directly in the subsequent step. LCMS (ES+) m/z 254, 256 (M+H)+,

Workup

  1. customThe precipitate was collected
  2. washwashed with water
  3. customdried at 50° C.

Sources & evidence

ORD record
ord-43d6af4d4a5844b0b73e0ab4b8c481a3
Source dataset
uspto-grants-2013_11
Patent number
US08591878B2

Reaction notes

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