Acetone → 1-(4-Bromophenyl)-4-ethoxybenzene

HRID 343461Notes

Reaction equation

HRID 343461 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:21][C:22](C)=O>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:21][CH3:22])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 950934-Bromo-4'-hydroxybiphenyl

Product 1

HCID 158408841-(4-Bromophenyl)-4-ethoxybenzeneYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-(4-bromophenyl)-phenol (4.06 g, 16.3 mmol) in acetone (30 mL) at room temperature, was added 4.5 eq K2CO3 (4.0M, 18 mL, 73.3 mmol) in water and 4.0 eq lodoethane (5.26 mL, 65.2 mmol). The reaction mixture was stirred overnight, and heated to reflux for 6 hrs. The product was crystallized out of the solution, and filtered. The crude product was recrystallized from hexane to provide ethyl 4-(4-bromophenyl) phenyl ether (4.1 g, 91%) as an white crystal.

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 hrs
  3. customThe product was crystallized out of the solution
  4. filtrationfiltered
  5. customThe crude product was recrystallized from hexane

Sources & evidence

ORD record
ord-b1ff756046424cdabb2334e260147684
Source dataset
uspto-grants-1999_01
Patent number
US05861428

Reaction notes

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