Methyl iodide → 2-Bromo-5-methoxy-1,3-dimethylbenzene

HRID 1872420Notes

Reaction equation

HRID 1872420 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].CI.[C:13](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOCC>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH3:13])=[CH:4][C:3]=1[CH3:10]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 819704-Bromo-3,5-dimethylphenol

Product 1

HCID 2359922-Bromo-5-methoxy-1,3-dimethylbenzene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of commercially available 4-bromo-3,5-dimethylphenol (a compound of Formula 4) (25.0 g, 124.3 mmol), methyl iodide (35.3 g, 248.6 mmol), and potassium carbonate (34.4 g, 248.6 mmol) in 62.5 mL of DMF was stirred for 2 hours at room temperature. The reaction mixture was diluted with 300 mL of ether and washed with 250 mL of water and 5×100 mL of brine. The organic portion was dried (MgSO4), filtered, and evaporated to give an oil, which was purified by flash column chromatography (silica gel, 90:10 hexane/ethylacetate) to give 4-bromo-3,5-dimethylanisole (a compound of Formula 5) (26 g, 120.8 mmol, 97%); 1HNMR (CDCl3) δ2.39 (s, 6H), 3.76 (s, 3H), 6.67 (s, 2H).

Workup

  1. washwashed with 250 mL of water and 5×100 mL of brine
  2. dry with materialThe organic portion was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto give an oil, which
  6. customwas purified by flash column chromatography (silica gel, 90:10 hexane/ethylacetate)

Sources & evidence

ORD record
ord-7d035fb659fb46cca57d0d7a22384f05
Source dataset
uspto-grants-2000_08
Patent number
US06107517

Reaction notes

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