Triphenylphosphine → 4-(Bromomethyl)picolinonitrile

HRID 619855Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 619855
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:22]([C:24]1[CH:29]=[C:28]([CH2:30]O)[CH:27]=[CH:26][N:25]=1)#[N:23]>C(Cl)Cl>[C:22]([C:24]1[CH:29]=[C:28]([CH2:30][Br:1])[CH:27]=[CH:26][N:25]=1)#[N:23]

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 107253914-(Hydroxymethyl)pyridine-2-carbonitrile

Produkt 1

HCID 106317764-(Bromomethyl)picolinonitrileAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Bromine (6.88 g, 43.1 mmol) is added dropwise to a solution of triphenylphosphine (11.3 g, 43.1 mmol) in 280 mL of CH2Cl2 at 0° C. The mixture is tirred for 30 minutes at 0° C. At this time, 2-cyano-4-(hydroxymethyl)-pyridine (4.82 g, 35.9 mmol) is added and the resulting mixture is stirred for 2 hours at room temperature. The reaction mixture is diluted with CH2Cl2 and washed with water (2x) and saturated NaCl solution. The organic layer is dried with MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting in a gradient of 20% EtOAc/hexanes to 30% EtOAc/hexanes to afford the title compound (6.40 g, 32.5 mmol) as an oil.

Aufarbeitung

  1. washwashed with water (2x) and saturated NaCl solution
  2. dry with materialThe organic layer is dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by column chromatography
  6. washeluting in a gradient of 20% EtOAc/hexanes to 30% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-2588eef75cfc4e2e94f71ede74c68103
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958918

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