Carbon tetrabromide → 2-(1-Bromopropyl)-6-chloropyridine

HRID 1048488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1048488
[Cl:1][C:2]1[N:7]=[C:6]([CH:8](O)[CH2:9][CH3:10])[CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:13][CH:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=1)[CH2:9][CH3:10]

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 585740021-(6-Chloropyridin-2-yl)propan-1-ol

Produkt 1

HCID 585733532-(1-Bromopropyl)-6-chloropyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 1-(6-chloropyridin-2-yl)propan-1-ol (0.497 g, 2.90 mmol), CBr4 (1.2 g, 3.62 mmol) and triphenylphosphine (0.987 g, 3.76 mmol) in 25 mL of THF was stirred at room temperature for 2 h. The solid was filtered off and washed with THF. The filtrate was concentrated and residue was purified by chromatography on silica gel, eluting with 10 to 50% EtOAc/hexane to provide the title compound. Mass Spectrum (ESI) m/z=236 (M+1).

Aufarbeitung

  1. filtrationThe solid was filtered off
  2. washwashed with THF
  3. concentrationThe filtrate was concentrated
  4. customresidue was purified by chromatography on silica gel
  5. washeluting with 10 to 50% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-b8247dbb772f4e389f7d85c2448ce531
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569341B2

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