Phosphorus oxybromide → Methyl 4-bromo-3-chloroquinoline-6-carboxylate

HRID 533416Notes

Reaction equation

HRID 533416 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1O)=[CH:9][C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=2.P(Br)(Br)([Br:19])=O>>[Br:19][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[CH:9]=2)[N:4]=[CH:3][C:2]=1[Cl:1]

Participants

3

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178497322HCID 178497322, compound

Product 1

HCID 67773454Methyl 4-bromo-3-chloroquinoline-6-carboxylateYield 56.1%

Conditions

Temperature
130 °C

Procedure

A mixture of methyl 3-chloro-4-hydroxyquinoline-6-carboxylate (600 mg) and phosphoryl bromide (868 mg) was heated under stirring in an oil bath at 130° C. for 6 hours. Ice-water was added, followed by neutralization with saturated aqueous sodium bicarbonate and extraction with ethyl acetate. The organic layer was washed with water, dried, and concentrated under reduced pressure to obtain methyl 4-bromo-3-chloroquinoline-6-carboxylate (426 mg).

Workup

  1. temperaturewas heated
  2. extractionfollowed by neutralization with saturated aqueous sodium bicarbonate and extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-667da52522404e4a9fded3d4372f430a
Source dataset
uspto-grants-2014_10
Patent number
US08853242B2

Reaction notes

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