Phosphorus oxide (P4O10) → 4-Bromo-8-methoxy-2-methylquinoline

HRID 1959550Notes

Reaction equation

HRID 1959550 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:13])[CH:9]=[C:8]2O.P(Br)(Br)([Br:17])=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[Br:17][C:8]1[C:7]2[C:12](=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][CH:6]=2)[N:11]=[C:10]([CH3:13])[CH:9]=1

Participants

4

Reactant 3

HCID 14812Phosphorus oxide (P4O10)HCID 24613Phosphorus oxybromideHCID 1784888088-Methoxy-2-methylquinolin-4-ol

Product 1

HCID 177505964-Bromo-8-methoxy-2-methylquinoline

Conditions

Temperature
120 °C

Procedure

8-Methoxy-2-methyl-quinolin-4-ol (9.0 g, 48 mmol) and POBr3 (53 g, 185 mmol) was placed in a round-bottomed flask, equipped with a drying tube containing P4O10. After stirring for 40 min at 120° C., the reaction mixture was cooled to room temperature and poured on ice. The mixture was then extracted with DCM (2×200 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with DCM/EA 10:1) to give the title compound. MS (m/z): 252.4 [M+H+].

Workup

  1. customequipped with a drying tube
  2. temperaturethe reaction mixture was cooled to room temperature
  3. additionpoured on ice
  4. extractionThe mixture was then extracted with DCM (2×200 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (elution with DCM/EA 10:1)

Sources & evidence

ORD record
ord-abe74678926045edad46ce51232e048f
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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