Carbon tetrabromide → 3-Bromo-methyl-5-trifluoromethyl-benzonitrile

HRID 604217Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604217
OC[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:6]#[N:7].[C:15]([Br:19])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:19][C:15]1[C:4]([CH3:3])=[C:5]([CH:8]=[C:9]([C:11]([F:12])([F:14])[F:13])[CH:10]=1)[C:6]#[N:7]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 117012213-(Hydroxymethyl)-5-(trifluoromethyl)benzonitrile

Produkt 1

HCID 666029993-Bromo-methyl-5-trifluoromethyl-benzonitrileAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Hydroxymethyl-5-trifluoromethyl-benzonitrile (23.4 g) is dissolved in methylene chloride (230 mL) and thereto is added carbon tetrabromide (42.4 g), followed by an addition of triphenylphosphine (32.0 g) under ice-cooling and the mixture is stirred at the same temperature for 30 minutes. The reaction solution is concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 3-bromo-methyl-5-trifluoromethyl-benzonitrile (25.5 g). NMR (CDCl3): 4.51 (2H, s), 7.86 (1H, s), 7.88 (2H, s)

Aufarbeitung

  1. temperaturecooling
  2. concentrationThe reaction solution is concentrated under reduced pressure
  3. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-f0f9af64c2324477a4db59d9f4b4d8b2
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906517B2

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