Boron tribromide → 2-Chloro-4-fluoroquinolin-6-ol

HRID 628897Notes

Reaction equation

HRID 628897 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:13]C)[CH:8]=2)[N:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:13])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 866899352-Chloro-4-fluoro-6-methoxyquinoline

Product 1

HCID 866899372-Chloro-4-fluoroquinolin-6-olYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture solution of 2-chloro-4-fluoro-6-methoxyquinoline (see U.S. 61/391,225 for synthesis) (280 mg, 1.32 mmol) and BBr3 (0.3 mL, 3.2 mmol, 2.64 g/mL) in DCM (5 mL) was stirred at 20° C. for 12 hours. Aqueous workup with DCM extraction gave the crude product, which was purified by silica gel column (PE/EtOAc=50/1) to give product (177 mg, yield 69%) as a white solid.

Workup

  1. extractionAqueous workup with DCM extraction
  2. customgave the crude product, which
  3. customwas purified by silica gel column (PE/EtOAc=50/1)

Sources & evidence

ORD record
ord-5c904c1096bc4331bbd31f2fa510cc11
Source dataset
uspto-grants-2016_04
Patent number
US09315462B2

Reaction notes

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