Boron tribromide → 3-Fluoro-4-methylphenol

HRID 2105975Notes

Reaction equation

HRID 2105975 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:9]C)[CH:5]=[CH:6][C:7]=1[CH3:8].B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 27745713-Fluoro-4-methylanisole

Product 1

HCID 27746133-Fluoro-4-methylphenolYield 75.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

To a −70° C. solution of 3-fluoro-4-methyl anisole (1.62 g; 11.6 mmol) in CH2Cl2 (10 mL) was added dropwise BBr3 (10 mL; 12 mmol). The reaction mixture was stirred at −70° C. for 10 min, then allowed to warm to 0° C. and stirred at 0° C. for 2 h. The reaction was allowed to warm to RT and concentrated in vacuo and the residue was partitioned between H2O and EtOAc. The organic phase was washed with H2O, dried (Na2SO4) and concentrated in vacuo to give 3-fluoro-4-methyl phenol (1.1 g; 75%) as an oil.

Workup

  1. temperatureto warm to 0° C.
  2. stirringstirred at 0° C. for 2 h
  3. temperatureto warm to RT
  4. concentrationconcentrated in vacuo
  5. customthe residue was partitioned between H2O and EtOAc
  6. washThe organic phase was washed with H2O
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1427a3896afb4d029cf924ceb8fd0caf
Source dataset
uspto-grants-2009_08
Patent number
US07579479B2

Reaction notes

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