Benzyl Bromide → 4-Bromo-6-chloro-2-methyl-1-benzyloxybenzene

HRID 842572Notes

Reaction equation

HRID 842572 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:4]([CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 820314-Bromo-6-chloro-o-cresol

Product 1

HCID 185046304-Bromo-6-chloro-2-methyl-1-benzyloxybenzeneYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 50 g of 4-bromo-6-chloro-2-methylphenol and 42.5 g of benzyl bromide dissolved in 200 ml of N,N-dimethylformamide was stirred at room temperature, to which 37.4 g of potassium carbonate was added, and the mixture was stirred for 12 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the residue was added to 400 ml of diethyl ether, washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 63 g of 4-bromo-6-chloro-2-methyl-1-benzyloxybenzene (90% yield).

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. customthe solvent was removed by distillation under reduced pressure
  4. additionthe residue was added to 400 ml of diethyl ether
  5. washwashed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto obtain a crude product

Sources & evidence

ORD record
ord-9f4dc948f8dc4e5ab6b23e4fbd14a507
Source dataset
uspto-grants-2002_04
Patent number
US06376428B1

Reaction notes

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