Reaktion #2156897

Reaktionsgleichung

2-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-chloro-benzaldehyde

IPA

NaBH4

→

title compound

Ausbeute 65.5%

6-tert-Butyl-2-(3-chloro-2-hydroxymethyl-phenyl)-8-fluoro-2H-phthalazin-1-one

Ausbeute 65.5%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting solution was cooled down to 4° C.
2. 2
   workup.STIRRINGAfter 30 min stirring
3. 3
   Sonstigethe reaction was quenched
4. 4
   workup.ADDITIONby adding H2O (200 mL)
5. 5
   SonstigeThe organic layer was collected by phase separation, and DCM
6. 6
   workup.DISTILLATIONwas distilled out from the solution
7. 7
   workup.ADDITIONwith adding additional IPA (1.6 L) in the same time at about 80° C
8. 8
   Sonstigeto crystallize out from IPA at around 30° C. with seeding
9. 9
   workup.ADDITIONwater (750 mL) was added to the solution dropwise
10. 10
    TemperaturThe resulting solution was cooled down to 5° C.
11. 11
    Filtrationfiltered
12. 12
    Sonstigeto collect the crystal material
13. 13
    WaschenThe filter cake was washed with IPA/water (2/1, 450 mL, pre-cooled to 5° C.)
14. 14
    Sonstigedried under vacuum oven at 65° C. overnight

Vorschrift

2-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-chloro-benzaldehyde (125 g, 0.35 mol) was dissolved in DCM (1 L) with stirring at room temperature, and then 0.5 L of IPA was added to the solution. The resulting solution was cooled down to 4° C., and NaBH4 (5.9 g, 0.16 mol) was added portion wise. After 30 min stirring, the reaction was quenched by adding H2O (200 mL). The organic layer was collected by phase separation, and DCM was distilled out from the solution with adding additional IPA (1.6 L) in the same time at about 80° C. The desired product started to crystallize out from IPA at around 30° C. with seeding, then water (750 mL) was added to the solution dropwise. The resulting solution was cooled down to 5° C. and filtered to collect the crystal material. The filter cake was washed with IPA/water (2/1, 450 mL, pre-cooled to 5° C.), and dried under vacuum oven at 65° C. overnight to afford 82.3 g of the title compound (65.5% isolated yield) as a white solid. MS (ESI) 360, 362 (M+H)+.

Quelle