Bromine → 2-Bromo-5,6-dimethoxy-3-methylbenzene-1,4-diol

HRID 2287258Notes

Reaction equation

HRID 2287258 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[C:11]([O:12][CH3:13])=[C:10]([OH:14])[C:9]([CH3:15])=[CH:8][C:6]=1[OH:7]>C(Cl)(Cl)Cl>[CH3:3][O:4][C:5]1[C:11]([O:12][CH3:13])=[C:10]([OH:14])[C:9]([CH3:15])=[C:8]([Br:1])[C:6]=1[OH:7]

Participants

4

Reactant 2

HCID 24408BromineHCID 111830272,3-Dimethoxy-5-methyl-1,4-benzenediol

Product 1

HCID 127215532-Bromo-5,6-dimethoxy-3-methylbenzene-1,4-diolYield 100.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 39.5 g of bromine in 70 ml of chloroform was added dropwise at about 5° C. to a solution of 46.0 g of 2,3-dimethoxy-5-methylhydroquinone in 500 ml of chloroform, under a nitrogen atmosphere. Stirring was continued at the same temperature for 3 hours, and then the reaction mixture was washed with water until the washings were colorless. The organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to provide 65.5 g of 2,3-dimethoxy-5-methyl-6-bromohydroquinone.

Workup

  1. washthe reaction mixture was washed with water until the washings
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-883910633b4440c3995129d0be420811
Source dataset
uspto-grants-1981_05
Patent number
US04270003

Reaction notes

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