Phosphorus oxybromide → HCID 86682940, compound

HRID 1497071Notes

Reaction equation

HRID 1497071 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([CH:17]([CH3:19])[CH3:18])=[N:7][C:8]2[C:13]([C:14]=1O)=[CH:12][C:11]([Cl:16])=[CH:10][CH:9]=2)=[O:4].P(Br)(Br)([Br:22])=O>C(Cl)Cl.O>[CH3:1][O:2][C:3]([C:5]1[C:6]([CH:17]([CH3:19])[CH3:18])=[N:7][C:8]2[C:13]([C:14]=1[Br:22])=[CH:12][C:11]([Cl:16])=[CH:10][CH:9]=2)=[O:4]

Participants

5

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178497915HCID 178497915, compound

Product 1

HCID 86682940HCID 86682940, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-chloro-4-hydroxy-2-isopropyl-quinoline-3-carboxylic acid methyl ester (800 mg, 2.86 mmol) in DCM (15 ml) was added POBr3 (1.23 g, 4.3 mmol) at 25° C. and the resulting reaction mixture was refluxed for 6 h. The reaction mixture was diluted with cold water, extracted with DCM, washed with brine, dried over sodium sulfate and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (eluting with 5% EtOAc in hexane on 100-200 mesh silica gel column chromatography) to afford pure 4-bromo-6-chloro-2-isopropyl-quinoline-3-carboxylic acid methyl ester (500 mg, 51%) as an off white solid. LC-MS: 343 (M+H)+.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 6 h
  3. extractionextracted with DCM
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a crude residue which
  8. customwas purified by flash column chromatography (eluting with 5% EtOAc in hexane on 100-200 mesh silica gel column chromatography)

Sources & evidence

ORD record
ord-cd3065edc3d7433380bedfa2bee195ad
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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