Boron tribromide → 2-Chloro-6-hydroxyquinoline-3-carbaldehyde

HRID 1620208Notes

Reaction equation

HRID 1620208 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14]C)[CH:8]=2)[N:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:14])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 6890792-Chloro-6-methoxyquinoline-3-carbaldehyde

Product 1

HCID 210510652-Chloro-6-hydroxyquinoline-3-carbaldehydeYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-6-methoxyquinoline-3-carbaldehyde (1.01 g, 4.54 mmol) in dry CH2Cl2 (36 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer at 0° C. under N2 was added dropwise BBr3 (1.0 N solution in CH2Cl2, 13.60 mL, 13.60 mmol). After complete addition, the bath was removed and stirring was continued overnight at RT. The reaction mixture was then added dropwise to a mixture of water and ice (50 mL) under stirring. After complete addition, the mixture was stirred for 30 min at RT and then filtered to give, after drying, 2-chloro-6-hydroxyquinoline-3-carbaldehyde as a yellow solid (0.77 g, 82% yield).

Workup

  1. additionAfter complete addition
  2. customthe bath was removed
  3. additionThe reaction mixture was then added dropwise to a mixture of water and ice (50 mL)
  4. stirringunder stirring
  5. additionAfter complete addition
  6. stirringthe mixture was stirred for 30 min at RT
  7. filtrationfiltered
  8. customto give
  9. customafter drying

Sources & evidence

ORD record
ord-c5ca210f7ff84ff4a081113922cd13e3
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

Loading…