Reaktion #70499

Reaktionsgleichung

1,4-dichloro-5,6,7,8-tetrahydro-phthalazine

4-fluoro-benzyl zinc chloride

→

1-chloro-4-(4-fluoro-benzyl)-5,6,7,8-tetrahydro-phthalazine

Ausbeute 74.9%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture is degassed
2. 2
   TemperaturThen the reaction mixture is cooled down to room temperature
3. 3
   workup.ADDITIONsat. NaHCO3 and water are added
4. 4
   Extraktionthe mixture is extracted with EtOAc
5. 5
   WaschenThe combined organic layers are washed with brine
6. 6
   Trocknendried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated down
9. 9
   SonstigeThe crude product is purified by chromatography (EtOAc/Hexane: 10%˜40%)

Vorschrift

To a solution of 1,4-dichloro-5,6,7,8-tetrahydro-phthalazine (0.50 g, 2.46 mmol) in THF (5 mL) are added 4-fluoro-benzyl zinc chloride (0.5M in THF) (6.40 mL, 3.20 mmol) and palladium tetrakis triphenylphosphine (0.36 g, 0.31 mmol). The mixture is degassed and stirred at 50° C. overnight. Then the reaction mixture is cooled down to room temperature, sat. NaHCO3 and water are added and the mixture is extracted with EtOAc. The combined organic layers are washed with brine, dried over Na2SO4, filtered and concentrated down. The crude product is purified by chromatography (EtOAc/Hexane: 10%˜40%) to give 1-chloro-4-(4-fluoro-benzyl)-5,6,7,8-tetrahydro-phthalazine (compound 10f) (0.51 g, 30%). m/z=277.11 [M+1]

Quelle