Phenol → 1-Bromo-2-(phenoxymethyl)benzene

HRID 229743Notes

Reaction equation

HRID 229743 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13]Br>CN(C)C=O>[Br:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][O:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 769652-Bromobenzyl bromide

Product 1

HCID 131696961-Bromo-2-(phenoxymethyl)benzeneYield 91.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.2 g of sodium hydride (at 50% in suspension in oil) are added at 5° C., in portions, to 20.2 g of phenol in solution in 150 ml of dimethylformamide. The mixture is stirred at room temperature and 37.2 g of 2-bromobenzyl bromide in solution in 15 ml of dimethylformamide are introduced at 5° C. After 2 hours at 20° C., the reaction medium is poured over ice-cold water and extracted with ethyl acetate. The organic phase is dried over anhydrous sodium sulphate and concentrated to give 36 g of oil.

Workup

  1. additionthe reaction medium is poured over ice-cold water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-90fc8a71b67740cdb2f5494f1fb77b11
Source dataset
uspto-grants-2009_07
Patent number
US07563903B2

Reaction notes

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