Methanol → 3-Fluoroquinolin-7-OL

HRID 1791659Notes

Reaction equation

HRID 1791659 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12]C)[CH:6]=2.B(Br)(Br)Br.CO>ClCCl>[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([OH:12])[CH:6]=2

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 220308563-Fluoro-7-methoxyquinoline

Product 1

HCID 1357631243-Fluoroquinolin-7-OL

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Fluoro-7-methoxyquinoline (130 mg, 0.74 mmol) was taken up in dichloromethane (2 ml) under nitrogen and treated with boron tribromide (4 ml of a 11.0M solution of in dichloromethane). The reaction mixture was stirred for 24 hours at ambient temperature followed by quenching the reaction by the slow addition of excess methanol. The solution was stirred for a further 2 hours and evaporated to dryness to give 3-fluoro-7-hydroxyquinoline which was used without further purification.

Workup

  1. customby quenching
  2. customthe reaction
  3. stirringThe solution was stirred for a further 2 hours
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-76e7e2024c9c4fb4b22242708b9a260b
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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