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

HRID 343480Notes

Reaction equation

HRID 343480 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 (4.0 M, 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-669d6def4a6547b6801e5722cf199e28
Source dataset
uspto-grants-1999_01
Patent number
US05861427

Reaction notes

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