Phosphorus oxybromide → Ethyl 4-bromoquinoline-2-carboxylate

HRID 1497315Notes

Reaction equation

HRID 1497315 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:3]=1.P(Br)(Br)([Br:19])=O>C1(C)C=CC=CC=1.C(#N)C>[Br:19][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:3]=1

Participants

5

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178469285HCID 178469285, compound

Product 1

HCID 21992780Ethyl 4-bromoquinoline-2-carboxylate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl 4-hydroxyquinoline-2-carboxylate (10.0 g, 46.0 mmol) and phosphorus oxybromide (13.2 g, 46.0 mmol) in 100 mL of toluene and 10.0 mL acetonitrile was heated at 75° C. for 1.5 h. The reaction mixture was cooled to room temperature, quenched slowly with water, and extracted with ethyl acetate. The organic fraction was washed with brine, dried over sodium sulfate, filtered, and concentrated. The resultant residue was subjected to silica gel chromatography eluting with 0-50% ethyl acetate in hexanes to afford ethyl 4-bromoquinoline-2-carboxylate that gave a mass ion (ES+) of 280.1 (79Br) for M+H+.

Workup

  1. customquenched slowly with water
  2. extractionextracted with ethyl acetate
  3. washThe organic fraction was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washeluting with 0-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-bf5239f09d5849a1858649a99f48d82b
Source dataset
uspto-grants-2015_12
Patent number
US09199939B2

Reaction notes

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