Methyl iodide → 4-Bromo-4'-methoxybiphenyl

HRID 352399Notes

Reaction equation

HRID 352399 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:15](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 950934-Bromo-4'-hydroxybiphenyl

Product 1

HCID 40340054-Bromo-4'-methoxybiphenylYield 623.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Part A: To a solution of 12.4 grams (5.0 mmol) of 4-(4′-bromophenyl)phenol in 50 mL of dimethylformamide was added 10.1 grams of potassium carbonate followed by 10.51 grams of iodomethane and this stirred at room temperature for 48 hours. The solution was diluted with 400 mL of water and extracted with ethyl acetate. The organics were dried over magnesium sulfate filtered and concentrated to yield 14.1 grams of crude product. Purification by recrystallization from ethyl acetate hexane gave 8.2 grams of 4-(4′-bromophenyl)anisole as a white crystalline solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield 14.1 grams of crude product
  6. customPurification
  7. customby recrystallization from ethyl acetate hexane

Sources & evidence

ORD record
ord-3d59836c57d244aa89afebaaa5ae3873
Source dataset
uspto-grants-2004_06
Patent number
US06747027B1

Reaction notes

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