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

HRID 481575Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 481575
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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 hr. 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 white crystals. 1H NMR (CDCl3) d 7.53 (d, J=8.83 Hz, 2H), 7.47 (d, J=6.62 Hz, 2H), 7.41 (d, J=8.46 Hz, 2H), 6.96 (d, J=8.82 Hz, 2H), 4.07 (q, J=6.99 Hz, 2H), 1.44 (t, J=6.99 Hz, 3H). ##STR254## Step 2

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-7a030b63bbcd44d2b7fe0e4f31a0a796
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05789434

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