Dimethylformamide → 4-Bromo-2-cyclobutoxy-1-methoxybenzene

HRID 2097470Notes

Reaction equation

HRID 2097470 reaction equation
[CH3:1]N(C)C=O.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([O:14][CH:15]2[CH2:18][CH2:17][CH2:16]2)[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].CI>O>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:1])=[C:9]([O:14][CH:15]2[CH2:18][CH2:17][CH2:16]2)[CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 666029544-Bromo-2-cyclobutoxyphenol

Product 1

HCID 581891134-Bromo-2-cyclobutoxy-1-methoxybenzeneYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 60 ml of N,N-dimethylformamide solution containing 6.22 g (25.6 mmol) of 4-bromo-2-cyclobutoxyphenol obtained in Reference Example 5-(d) were successively added 3.54 g of potassium carbonate and 3.2 ml of methyl iodide, and the mixture was stirred at room temperature for 6 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with toluene. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; toluene), and the obtained crude solid was recrystallized from hexane to obtain 3.90 g of the title compound as a colorless solid. (Yield: 59%)

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with toluene
  3. customThe organic layer after separation
  4. washwas washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe obtained crude solid
  8. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-4cd84fe83a1a4157b7fe9d1cfad5ecd5
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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