Boron tribromide → 3-Isobutyryl-4-chloro-8-hydroxyquinoline

HRID 1647480Notes

Reaction equation

HRID 1647480 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:16])=[CH:13][CH:12]=[CH:11][C:10]=2[O:17]C)(=[O:5])[CH:2]([CH3:4])[CH3:3].B(Br)(Br)Br>ClCCl>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:16])=[CH:13][CH:12]=[CH:11][C:10]=2[OH:17])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 100841433-Isobutyryl-4-chloro-8-methoxyquinoline

Product 1

HCID 199230183-Isobutyryl-4-chloro-8-hydroxyquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-isobutyryl-4-chloro-8-methoxy-quinoline (21.1 g, 80 mmol) in dichloromethane (320 ml) was cooled to -10° and boron tribromide (60.13 g, 240 mmol) added dropwise under nitrogen. The solution was allowed to warm to room temperature, and after 16 hours was poured onto crushed ice (500 g). The layers were separated, and the aqueous layer further extracted with dichloromethane. The combined extracts were washed with brine, dried and evaporated to a yellow solid (29.75 g). This complex of 3-isobutyryl-4-chloro-8-hydroxyquinoline was used without further purification.

Workup

  1. additionafter 16 hours was poured
  2. customThe layers were separated
  3. extractionthe aqueous layer further extracted with dichloromethane
  4. washThe combined extracts were washed with brine
  5. customdried
  6. customevaporated to a yellow solid (29.75 g)
  7. customThis complex of 3-isobutyryl-4-chloro-8-hydroxyquinoline was used without further purification

Sources & evidence

ORD record
ord-76b66c2a214b4c359247b0d095344b50
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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