Triphenylphosphine → 4-Bromo-2-(bromomethyl)-1-fluorobenzene

HRID 2780

Reaktionsgleichung

Reaktionsgleichung von HRID 2780
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH2:7]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:30]N1C(=O)CCC1=O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH2:7][Br:30]

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 2773352(5-Bromo-2-fluorophenyl)methanol

Produkt 1

HCID 135532954-Bromo-2-(bromomethyl)-1-fluorobenzeneAusbeute 96,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-bromo-2-fluoro-benzyl alcohol (3.10 g, 15.1 mmol) in 30 mL of THF at 10° C. is added triphenyl phosphine (4.10 g, 15.6 mmol) followed by N-bromosuccinimide (2.67 g, 15.0 mmol). The ice bath is removed and the resulting solution is stirred for 20 min at room temperature. The crude product is purified by column chromatography eluting with 5% EtOAc/hexanes to give the title compound (3.90 g, 14.5 mmol).

Aufarbeitung

  1. customThe ice bath is removed
  2. customThe crude product is purified by column chromatography
  3. washeluting with 5% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-01265d1ee5214b12aaf7fb783abeb10c
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731315

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