Methanol → 3-Fluoroquinolin-7-OL

HRID 454134Notes

Reaction equation

HRID 454134 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 1.0M 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-9ecadf86ec4b4c428f8e3746328eae92
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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