Benzyl Chloride → 1-(Benzyloxy)-3-bromobenzene

HRID 1455901Notes

Reaction equation

HRID 1455901 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH2:9](Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:9]([O:8][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 115633-Bromophenol

Product 1

HCID 27566381-(Benzyloxy)-3-bromobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A slurry of 3-bromophenol 100 g (580 mmol), benzylchloride 80 g (700 mmol), and K2CO3 168 g (1210 mmol) in 2 L of DMF was stirred for sixteen hour at ambient temperature. The reaction mixture was filtered and evaporated to dryness. The solid was partioned between CHCl3 and water. The organic layer was separated, washed twice with brine, and dried by filtration through anhydrous Na2SO4. The solution was evaporated to dryness. This yielded 142.5 g of the title compound as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to dryness
  3. customThe organic layer was separated
  4. washwashed twice with brine
  5. dry with materialdried by filtration through anhydrous Na2SO4
  6. customThe solution was evaporated to dryness

Sources & evidence

ORD record
ord-17ce53964a384ee9b6dc841021b3d8dc
Source dataset
uspto-grants-1998_12
Patent number
US05843940

Reaction notes

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