Boron tribromide → 6-Methoxyquinolin-8-ol

HRID 987578Notes

Reaction equation

HRID 987578 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:13]C)[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.B(Br)(Br)Br>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([OH:13])[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 180091746,8-Dimethoxyquinoline

Product 1

HCID 180091706-Methoxyquinolin-8-olYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-25 °C

Procedure

To a −25° C. solution of 3.0 g (15.9 mmol) 6,8-dimethoxyquinoline and 160 mL CH2Cl2 is added 16 mL (15.9 mmol) of 1M BBr3 in CH2Cl2. After stirring for 2 h at −25° C., the reaction mixture is quenched with 300 mL of H2O, the layers separated in a separatory funnel, and the aqueous extracted with CH2Cl2 (2×100 mL). The combined organics are washed with 1×100 mL H2O, 1×100 mL brine, dried over MgSO4, filtered, and the volatiles are evaporated. Flash chromatography on SiO2, eluting with 3/1 EtOAc/hexanes containing 10% MeOH, gives 0.96 g (5.48 mmol, a 34% yield) of the title compound as an tan solid. MS (ES) m/z 176 (MH)+.

Workup

  1. customthe reaction mixture is quenched with 300 mL of H2O
  2. customthe layers separated in a separatory funnel
  3. extractionthe aqueous extracted with CH2Cl2 (2×100 mL)
  4. washThe combined organics are washed with 1×100 mL H2O, 1×100 mL brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe volatiles are evaporated
  8. washFlash chromatography on SiO2, eluting with 3/1 EtOAc/hexanes containing 10% MeOH
  9. customgives 0.96 g (5.48 mmol

Sources & evidence

ORD record
ord-137b7cf2b0c6407c9bc576f5e3ce7b45
Source dataset
uspto-grants-2003_10
Patent number
US06632824B2

Reaction notes

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