Phosphorus tribromide → 4-Bromo-6-methoxyquinoline

HRID 1435843Notes

Reaction equation

HRID 1435843 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:15]>CN(C=O)C>[Br:15][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 178487890HCID 178487890, compound

Product 1

HCID 111607474-Bromo-6-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-hydroxy-6-methoxyquinoline (1.20 g, 70.5 mmole) in DMF (60 mL) at RT was added PBr3 (8.0 mL, 84.6 mmole) dropwise. After 2 h, the reaction contents were poured onto H2O (300 mL) and the product filtered and washed with H2O to give, after drying under high vacuum, the title compound (14.3 g, 87%) as a light yellow solid: LC-MS (ES) m/e 233 (M+H)+.

Workup

  1. customthe reaction contents
  2. additionwere poured onto H2O (300 mL)
  3. filtrationthe product filtered
  4. washwashed with H2O
  5. customto give
  6. customafter drying under high vacuum

Sources & evidence

ORD record
ord-d52f1c912b9c41c6bcf52ebbeb797013
Source dataset
uspto-grants-2009_11
Patent number
US07618959B2

Reaction notes

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