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

HRID 363534Notes

Reaction equation

HRID 363534 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+].I[CH2:22][CH3:23]>CC(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][CH2:22][CH3:23])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 950934-Bromo-4'-hydroxybiphenyl

Product 1

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

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 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 Iodoethane (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-05409c6f304b45aaace1dbf5090fa155
Source dataset
uspto-grants-1999_02
Patent number
US05874473

Reaction notes

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