Boron tribromide → HCID 19603385, compound

HRID 1604573Notes

Reaction equation

HRID 1604573 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([O:12]C)[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:14])[C:3]=1[CH3:15].B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:14])[C:3]=1[CH3:15]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 15458589HCID 15458589, compound

Product 1

HCID 19603385HCID 19603385, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-2,3-dimethyl-8-methoxyquinoline (2.5 g) in dichloromethane (5 ml) was added boron tribromide (22.6 ml) under ice-cooling, and the mixture was stirred for 3 hours. The reaction mixture was extracted with 10% solution of methanol in chloroform, and the organic layer was dried over magnesium sulfate and concentrated. The residue was dissolved in acetonitrile under heating, and the mixture was allowed to cool. The resulting precipitates were collected by filtration to give 4-chloro-2,3-dimethyl-8-hydroxyquinoline (1.50 g).

Workup

  1. temperaturecooling
  2. extractionThe reaction mixture was extracted with 10% solution of methanol in chloroform
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in acetonitrile
  6. temperatureunder heating
  7. temperatureto cool
  8. customThe resulting precipitates
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-e8a7996c98df4aa5b14f7cc734e81c78
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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