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

HRID 1418764Notes

Reaction equation

HRID 1418764 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-dimethylbenzeneYield 97.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-bromo-3,5-dimethylphenol (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 (5) (26 g, 120.8 mmol, 97%); 1HNMR (CDCl3) δ 2.39 (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-795019103aa447e2990e3856c7e9e842
Source dataset
uspto-grants-1999_03
Patent number
US05883294

Reaction notes

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