Dichloromethane → 5-(Prop-1-en-2-yl)-2-(trifluoromethyl)pyridine

HRID 607501Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 607501
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1.[C:12]([B-](F)(F)F)([CH3:14])=[CH2:13].[K+].C(Cl)Cl.C(N(CC)CC)C>C(O)CC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:12]([C:2]1[CH:3]=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1)([CH3:14])=[CH2:13]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 27611975-Bromo-2-(trifluoromethyl)pyridineHCID 23670158Potassium (prop-1-en-2-yl)trifluoroborate

Produkt 1

HCID 576623365-(Prop-1-en-2-yl)-2-(trifluoromethyl)pyridineAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 10311-PropanolLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-2-(trifluoromethyl)pyridine (452 mg, 2.0 mmol), potassium isopropenyltrifluoroborate (355 mg, 2.4 mmol), PdCl2(dppf).CH2Cl2 (82 mg, 0.1 mmol) and triethylamine (0.28 ml, 2.0 mmol) in n-propanol (20 ml) was treated in the same procedure as described in Example 10B. The crude residue was applied to a silica gel chromatography column and eluted with a volume mixture of hexane and EtOAc (20/1) to afford 219 mg (59% yield) of the title compound as a colorless oil.

Aufarbeitung

  1. washeluted with a volume mixture of hexane and EtOAc (20/1)

Quellen und Nachweise

ORD-Eintrag
ord-7962a2bc178e45cd9c1e63031377fa83
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915448B2

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