Methanol → alpha-(Aminomethyl)-3,4-dichlorobenzenemethanol

Temperatur

0 °C

To a mixture of 3,4-dichlorobenzaldehyde (3.50 g, 20.2 mmol) and ZnI2 (19 mg, 0.06 mmol) at 0° C. was added TMSCN (2.2 g, 2.2 mmol). The reaction mixture was stirred at 0° C. for 10 min and then warmed to rt and stirred for an additional 1 h. The mixture was concentrated to afford an orange-brown colored oil. The oil was dissolved in THF (20 mL) and BH3.THF (1 M in THF; 25 mL, 25 mmol) was added at 0° C. The reaction mixture was warmed to rt and stirred overnight. The mixture was cooled to 0° C. and MeOH (6 mL) was added with continued stirring for 2 h. After being warmed to rt, the mixture was concentrated. The residue was dissolved in MeOH (10 mL) and HCl (2 M in Et2O; 25 mL) was added at 0° C. After 30 min, Et2O (100 mL) was added and the resulting white solid was filtered and washed with Et2O (2×50 mL) to give a white solid (3.5 g, 72%).

1. temperaturewarmed to rt
2. stirringstirred for an additional 1 h
3. concentrationThe mixture was concentrated
4. customto afford an orange-brown colored oil
5. temperatureThe reaction mixture was warmed to rt
6. stirringstirred overnight
7. temperatureThe mixture was cooled to 0° C.
8. stirringwith continued stirring for 2 h
9. temperatureAfter being warmed to rt
10. concentrationthe mixture was concentrated
11. dissolutionThe residue was dissolved in MeOH (10 mL)
12. additionHCl (2 M in Et2O; 25 mL) was added at 0° C
13. waitAfter 30 min
14. additionEt2O (100 mL) was added
15. filtrationthe resulting white solid was filtered
16. washwashed with Et2O (2×50 mL)

ORD-Eintrag

ord-0689aa7f7264494d988f565bb322fb78

Quelldatensatz

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08598202B2