Phosphorus oxybromide → 2-Bromo-6-methoxyquinoline

HRID 2045715Notes

Reaction equation

HRID 2045715 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=O)[CH:7]=[CH:6]2.P(Br)(Br)([Br:16])=O>>[Br:16][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=1

Participants

3

Reactant 2

HCID 24613Phosphorus oxybromideHCID 2282682-Hydroxy-6-methoxyquinoline

Product 1

HCID 114704222-Bromo-6-methoxyquinolineYield 49.3%

Conditions

Temperature
140 °C

Procedure

6-Methoxyquinolin-2(1H)-one (6.81 g, 38.9 mmol) was carefully added to POBr3 (18.9 g, 66.1 mmol) at 60° C., and the resulting solution was stirred at 140° C. for 2.5 h. The reaction mixture was cooled and poured onto crushed ice, and the solid was collected by filtration. Purification of this material on silica gel (gradient elution from 5 to 12% EtOAc in petroleum ether) afforded the title compound (4.57 g, 49.3%) as a solid. LCMS (ES+) m/z 238, 240 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionpoured
  3. customonto crushed ice
  4. filtrationthe solid was collected by filtration
  5. customPurification of this material on silica gel (gradient elution from 5 to 12% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-9042e30c9dd44a0ea7cfddb3ec75d3e9
Source dataset
uspto-grants-2013_11
Patent number
US08591878B2

Reaction notes

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