(2-Bromopyridine)-(2-chlorophenyl)-methanol → (2-Bromopyridin-3-yl)-(2-chlorophenyl)methanone

HRID 2251958

Reaktionsgleichung

Reaktionsgleichung von HRID 2251958
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][OH:9].[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1>C1(C)C=CC=CC=1.[O-2].[Mn+4].[O-2]>[Br:10][C:11]1[C:16]([C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[O:9])=[CH:15][CH:14]=[CH:13][N:12]=1

Komponenten

4

Edukt 1

HCID 86601242(2-Bromopyridine)-(2-chlorophenyl)-methanol

Produkt 1

HCID 85882881(2-Bromopyridin-3-yl)-(2-chlorophenyl)methanoneAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Add 85% manganese(IV) oxide (500 g, 5.75 mol) to a slurry of (2-bromopyridine)-(2-chlorophenyl)-methanol (392 g, 1.131 mol) in toluene (2.5 L), heat to a reflux and stir. After one hour cool to ambient temperature and filter through Celite®. Concentrate the solution under reduced pressure. Purify by recrystalization from MTBE: heptane (2:1) to give title compound 312.4 g (80%). 1H NMR (300 MHz, CDCl3), δ 8.50 (dd, 1H, J=1.83, 4.73), 7.78 (dd, 1H, J=1.83, 7.63), 7.60 (dd, 1H, J=1.53, 7.63), 7.53-7.34 (m, 4H); MS (IS) m/z 296.0 (M+1), 298.0 (M+1); m.p.=76.3° C.; Analysis for C12H7BrClNO: calcd: C, 48.60; H, 2.38; N, 4.72; found: C, 48.71; H, 2.48; N, 4.61; Rf=0.40 (hexane:ethyl acetate 2:1).

Aufarbeitung

  1. temperatureheat to
  2. temperaturea reflux
  3. filtrationfilter through Celite®
  4. concentrationConcentrate the solution under reduced pressure
  5. customPurify by recrystalization from MTBE: heptane (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-d63db0047d4241ceb06170c272af5901
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07320994B2

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