Réaction #70499

Équation de réaction

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

Rendement 74.9%

Solvants

THF

Conditions de réaction

Traitement

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

Mode opératoire

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]

Source