Imidazole → 4-(2-Bromoethyl)-2-fluoro-1-methoxybenzene

HRID 1810015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1810015
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[Br:25]Br.O[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([F:38])[CH:31]=1>C(Cl)Cl>[Br:25][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[C:32]([F:38])[CH:31]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 24408BromineHCID 27589993-Fluoro-4-methoxyphenethyl alcohol

Produkt 1

HCID 534041114-(2-Bromoethyl)-2-fluoro-1-methoxybenzeneAusbeute 59,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of resin bound triphenyl phosphine (polystyrene 2% cross linking, loading=3 mmol/g, 3 g, 9 mmol) and imidazole (0.48 g, 7.1 mmol) in DCM (30 mL) cooled on an ice bath was drop wise added Br2 (1.13 g, 7.1 mmol), whereupon a solution of 4-(2-hydroxy-ethyl)-2-fluoro-1-methoxy-benzene (1.0 g, 5.88 mmol) in DCM (5 mL) was added. The cooling bath was removed and the reaction mixture was stirred for 16 hs before the resin was filtered off. The resin was washed with DCM and the filtrate was concentrated in vacuo. The residue was purified using column chromatography (SiO2, heptane-EtAOc 95:5) to give 0.82 g of 4-(2-bromo-ethyl)-2-fluoro-1-methoxy-benzene

Aufarbeitung

  1. additionA mixture of resin
  2. temperaturecooled on an ice bath
  3. customThe cooling bath was removed
  4. filtrationwas filtered off
  5. washThe resin was washed with DCM
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-c0551eb6173e456eae4efd5ae274f767
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362049B2

Notizen zur Reaktion

Wird geladen…