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

HRID 1620303Notes

Reaction equation

HRID 1620303 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 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-chloro-6-methoxyquinoline-3-carbaldehyde (5.27 g, 23.8 mmol) in anhydrous CH2Cl2 (180 mL) in a 500 mL round-bottomed flask equipped with a magnetic stirrer was added dropwise BBr3 (71.3 mL, 71.3 mmol) at 0° C. and the mixture was stirred at RT overnight. The mixture was then added dropwise to a water/ice mixture, and the solid was filtered and dried under vacuum to give 2-chloro-6-hydroxyquinoline-3-carbaldehyde SLA 47016 as a yellow solid (3.14 g, 64% yield).

Workup

  1. filtrationthe solid was filtered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-c098add6e59842f0a2d104c8bad2f8d5
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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