Carbon Tetrachloride → 2-Bromo-4-chloroanisole

HRID 1017241Notes

Reaction equation

HRID 1017241 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5]C=[CH:3][CH:2]=1.[Br:9]Br.[C:11]([Cl:15])(Cl)(Cl)Cl>[Fe]>[Br:9][C:2]1[CH:3]=[C:11]([Cl:15])[CH:5]=[CH:6][C:1]=1[O:7][CH3:8]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 7519AnisoleHCID 24408Bromine

Product 1

HCID 5219352-Bromo-4-chloroanisole

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Anisole (10 g, 70.1 mmol) was dissolved in carbon tetrachloride (200 ml) and iron powder (6.0 g, 105 mmol Fe)was added. Bromine (4 ml, 77.1 mmol) was added at 0° C. The temperature was allowed rise to room temperature over one hour. Washing with aqueous sodium sulfite three times was followed by washing with aqueous sodium hydroxide (4 M). Drying over magnesium sulfate and evaporation gave the title compound. Yield 5.63 g, 36%.

Workup

  1. customto room temperature
  2. customover one hour
  3. washWashing with aqueous sodium sulfite three times
  4. washby washing with aqueous sodium hydroxide (4 M)
  5. dry with materialDrying over magnesium sulfate and evaporation

Sources & evidence

ORD record
ord-9fe0ff3d98e3482a8d00ac042baa29c9
Source dataset
uspto-grants-2002_11
Patent number
US06479491B1

Reaction notes

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