Benzyl Bromide → HCID 86747042, compound

HRID 484547Notes

Reaction equation

HRID 484547 reaction equation
[OH-:1].[K+].[Br:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1O.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CS(C)=O>[Br:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[CH:12]([O:1][CH:12]([C:5]1[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:4]=1[Br:3])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 696702-Bromo-4-chlorophenol

Product 1

HCID 86747042HCID 86747042, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

In a 500 ml three neck round bottom flask equipped with a magnetic stirrer, thermometer, condenser, addition funnel and nitrogen inlet, is placed 30 ml of dimethylsulfoxide. Potassium hydroxide (20 g, 0.36 mol.) is added to this followed by the dropwise addition of 2-bromo-4-chlorophenol (50 g, 0.24 mol) in 25 ml of dimethylsulfoxide. This solution is stirred for half an hour, then benzylbromide (41 g, 0.24 mol) is added dropwise, and the reaction stirred for another 3 hours. The reaction is then poured into 150 ml of ice water and extracted with 100 ml of toluene. The toluene phase is washed with 50 ml of 1N sodium hydroxide followed by 75 ml of water, dried with magnesium sulfate and evaporated under reduced pressure to yield 65 g of 2-bromo-4-chlorophenyl benzylether.

Workup

  1. additionthermometer, condenser, addition funnel and nitrogen inlet
  2. stirringthe reaction stirred for another 3 hours
  3. extractionextracted with 100 ml of toluene
  4. washThe toluene phase is washed with 50 ml of 1N sodium hydroxide
  5. dry with materialdried with magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2eb338f5448b4ee88b669d0e853f881e
Source dataset
uspto-grants-1993_07
Patent number
US05231198

Reaction notes

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