Ethanol → 1,2-Bis(4-bromophenyl)-2-hydroxyethanone

HRID 1595952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1595952
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(N([CH2:15][CH3:16])CC)C.[CH2:17]([OH:19])[CH3:18]>[Br-].C([N+]1C(C)=C(CCO)SC=1)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([CH:17]([C:18]2[CH:16]=[CH:15][C:2]([Br:1])=[CH:3][CH:4]=2)[OH:19])=[O:7])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 8471TriethylamineHCID 707414-Bromobenzaldehyde

Produkt 1

HCID 39382431,2-Bis(4-bromophenyl)-2-hydroxyethanoneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromideKatalysator

Versuchsvorschrift

A solution of 4-bromobenzaldehyde (25.0 g, 0.135 mol), 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (1.70 g, 0.0068 mol) and triethylamine (4.10 g, 0.0405 mol) in ethanol (125 mL) is stirred at room temperature for 60 hours. The reaction mixture is concentrated to dryness, then taken up in CH2Cl2 (150 mL), washed with 1 M HCl and saturated aqueous NaHCO3 and dried (Na2SO4), then concentrated, giving 25.2 g (100 percent) of a viscous yellow oil which solidifies upon standing at room temperature. 1H NMR (CDCl3) δ 7.73 (d, J=8.5 Hz, 2H), δ 7.52 (d, J=8.5 Hz, 2H), 7.44 (d, J=8.2 Hz, 2H), 7.17 (d, J=8.2 Hz, 2H) 13C NMR (CDCl3) δ 197.33, 137.56, 132.33, 132.13, 131.90, 130.43, 129.46, 129.31, 122.93, 75.68.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated to dryness
  2. washwashed with 1 M HCl and saturated aqueous NaHCO3
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-85965dbd71ed4b318b4d8901b5404da1
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06288188B1

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