Bromine → 4-Bromo-2,6-dimethylanisole

HRID 893005Notes

Reaction equation

HRID 893005 reaction equation
[Br:1]Br.[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[O:11][CH3:12]>C(Cl)(Cl)Cl>[CH3:3][C:4]1[CH:9]=[C:8]([Br:1])[CH:7]=[C:6]([CH3:10])[C:5]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 24408BromineHCID 660882,6-Dimethylanisole

Product 1

HCID 2786544-Bromo-2,6-dimethylanisole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Bromine is added dropwise to a solution of 2,6-dimethylanisole (12.0 g) in chloroform (100 ml) at about 5°. The solution is stirred at 5° for 2 hr and then allowed to warm to 20°-25°. The reaction mixture is poured into ice-water, and the phases are separated. The chloroform phase is washed with water, aqueous sodium bisulfite solution, then with water, dried over sodium sulfate and concentrated under reduced pressure to give 3,5-dimethyl-4-methoxybromobenzene.

Workup

  1. temperatureto warm to 20°-25°
  2. customthe phases are separated
  3. washThe chloroform phase is washed with water, aqueous sodium bisulfite solution
  4. dry with materialwith water, dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb0ab77301744fde94585094b7cdac40
Source dataset
uspto-grants-1992_06
Patent number
US05120843

Reaction notes

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