Boron tribromide → HCID 10263493, compound

HRID 1534502Notes

Reaction equation

HRID 1534502 reaction equation
[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[Cl:15])=[CH:12][CH:11]=[CH:10][C:9]=2[O:16]C)(=[O:4])[CH2:2][CH3:3].B(Br)(Br)Br>ClCCl>[C:1]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[Cl:15])=[CH:12][CH:11]=[CH:10][C:9]=2[OH:16])(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10377394HCID 10377394, compound

Product 1

HCID 10263493HCID 10263493, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Propanoyl-4-chloro-8-methoxyquinoline (32 g) was dissolved in dichloromethane (250 ml), cooled to -78°, and boron tribromide (37 ml) added slowly. The solution was allowed to warm slowly to room temperature overnight, then recooled in ice and quenched cautiously with water. The resulting solid was filtered off and washed with water to give crude 3-propanoyl-4-chloro-8-hydroxyquinoline (115 g crude weight), which was used without further purification.

Workup

  1. temperaturecooled to -78°
  2. customquenched cautiously with water
  3. filtrationThe resulting solid was filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-0398bb8997df4e7ebada86a1ce2f29c4
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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