Methyl iodide → 4-Bromo-1-methoxy-2-methylbenzene

HRID 1839949Notes

Reaction equation

HRID 1839949 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.[C:10]([O-])([O-])=O.[K+].[K+].IC>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:10])=[C:4]([CH3:9])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 168964-Bromo-2-methylphenol

Product 1

HCID 6083154-Bromo-1-methoxy-2-methylbenzeneYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen, to a stirred suspension of 38.9 g (208 mmol) of 4-bromo-2-methylphenol and 43.1 g (312 mmol) of K2CO3 powder in 300 mL of THF was added 39 mL (624 mmol) of iodomethane. The mixture was heated to reflux overnight, and cooled to ambient temperature. The inorganic salts were removed by filtration, and the organic solvent was removed in vacuo. The residue was dissolved in ethyl acetate, washed with water and brine, and dried over MgSO4. Purification by silica gel plug with ethyl acetate/hexane (5:95) gave 28 g (67%) of 4-bromo-2-methylanisole as a colorless solid: mp 65.0-66.0° C.; NMR (CDCl3) δ 2.18 (s, 3H), 3.80 (s, 3H), 6.67 (d, J=9 Hz, 1H), 7.22-7.28 (m, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customThe inorganic salts were removed by filtration
  4. customthe organic solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with water and brine
  7. dry with materialdried over MgSO4
  8. customPurification by silica gel plug with ethyl acetate/hexane (5:95)

Sources & evidence

ORD record
ord-d12ec91f44eb44df8a655fb05d13847a
Source dataset
uspto-grants-2004_01
Patent number
US06677488B2

Reaction notes

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