Methyl iodide → 1-Bromo-3-methoxy-5-methylbenzene

HRID 530424

Reaction equation

HRID 530424 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:10]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 126484093-Bromo-5-methylphenol

Product 1

HCID 106795541-Bromo-3-methoxy-5-methylbenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 3-bromo-5-methyl-phenol (185 g; 0.940 mol) and K2CO3 (437 g, 3.17 mol) in acetone (2 L) is added MeI (424 g, 2.99 mol). The mixture is stirred at 40° C. for 16 h. The mixture is cooled to ambient temperature, filtered, and concentrated under reduced pressure. After filtration, the mixture is purified by flash silica gel chromatography to afford 1-Bromo-3-methoxy-5-methyl-benzene, D-4-1 (189 g, quant. yield) as a light yellow oil.

Workup

  1. temperatureThe mixture is cooled to ambient temperature
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. filtrationAfter filtration
  5. customthe mixture is purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-f1abf1cb0fbf45569dbaa2de7aab9ac4
Source dataset
uspto-grants-2016_05
Patent number
US09353090B2

Linked notes

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