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

HRID 369681Notes

Reaction equation

HRID 369681 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH2:10][CH3:11])[CH:3]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([CH2:10][CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 220068384-Bromo-2-ethyl-6-methylphenol

Product 1

HCID 220068134-Bromo-2-ethyl-6-methyl-1-benzyloxybenzeneYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 26 g of 4-bromo-2-ethyl-6-methylphenol, 24.8 g of benzyl bromide and 200 ml of N,N-dimethylformamide was added 21.7 g of potassium carbonate with stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was poured into ice water and extracted twice with 500 ml of diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and then concentrated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 35.6 g of 4-bromo-2-ethyl-6-methyl-1-benzyloxybenzene (yield, 97%).

Workup

  1. stirringAfter stirring at room temperature for 24 hours
  2. extractionextracted twice with 500 ml of diethyl ether
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto give a crude product

Sources & evidence

ORD record
ord-bf7f8a4897754d8ea89d0b342163026e
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Reaction notes

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