Phosphorus tribromide → 4-Bromomethyl-2,6-dimethyl-4'-trifluoromethyl-biphenyl

HRID 251309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 251309
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=[C:4]([CH3:10])[C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1.P(Br)(Br)[Br:22]>C1COCC1>[Br:22][CH2:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[C:4]([CH3:10])[CH:5]=1

Komponenten

4

Edukt 2

HCID 24614Phosphorus tribromideHCID 67485876HCID 67485876, Verbindung

Produkt 1

HCID 674861454-Bromomethyl-2,6-dimethyl-4'-trifluoromethyl-biphenylAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of (2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yl)-methanol (2.22 g, 7.9 mmol) in THF (30 ml) is added PBr3 (3.22 g, 11.9 mmol) in THF (5 ml) and the reaction is allowed to stir at room temperature for about 2 h. The reaction is cooled to 0° C. and ice water is added slowly. The mixture is extracted with ethyl acetate, dried over MgSO4, and concentrated. The resulting residue is purified by silica gel column chromatography, eluting with EtOAc/hexanes to afford 2.2 g of the titled compound as a white solid. 1H-NMR.

Aufarbeitung

  1. temperatureThe reaction is cooled to 0° C.
  2. extractionThe mixture is extracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe resulting residue is purified by silica gel column chromatography
  6. washeluting with EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ca9b35e2ff434e9289f4c5e40d6eda67
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863329B2

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