Benzyl Chloride → 1-Bromo-4-phenylmethoxybenzene

HRID 2050944Notes

Reaction equation

HRID 2050944 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9](Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7503Benzyl ChlorideHCID 78084-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 1388351-Bromo-4-phenylmethoxybenzeneYield 65%

Procedure

4-Bromophenol (17.3 g, 0.1 mol), 19.03 g (0.15 mol) benzyl chloride, and 27.64 g (0.2 mol) pulverized K2CO3 were suspended in 150 mL Me2CO and heated to reflux 2 h. The resulting suspension was concentrated on a rotary evaporator. The mixture was then diluted with 200 mL 5% NaOH and extracted with 100 mL Et2O. The organic layer was washed with an additional 100 mL 5% NaOH, dried (MgSO4), filtered, and concentrated to give a yellow oil, which was crystallized and recrystallized from boiling EtOH to yield 17 g (65%) of Benzyl 4-bromo phenyl ether as white needles, mp: 60°-61° C. NMR δ 7.35 and 6.82 (AA'BB', c, 4H, C6H4), 7.36 (s, 5H, C6H5), 5.0 (s, 2H, OCH2).

Workup

  1. temperatureheated
  2. temperatureto reflux 2 h
  3. concentrationThe resulting suspension was concentrated on a rotary evaporator
  4. additionThe mixture was then diluted with 200 mL 5% NaOH
  5. extractionextracted with 100 mL Et2O
  6. washThe organic layer was washed with an additional 100 mL 5% NaOH
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a yellow oil, which
  11. customwas crystallized
  12. customrecrystallized

Sources & evidence

ORD record
ord-58c30ec4688f41afbfd5cce9cce69a54
Source dataset
uspto-grants-1991_05
Patent number
US05015666

Reaction notes

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