Hydrochloric Acid → 3,4-Difluorobenzylamine

Temperature

45 °C

To THF (18 ml) was added cerium(III) chloride (2.84 g, 11.50 mmol) and the solution was purged, backfilled with nitrogen and warmed to 45° C. for 3 h. The reaction was cooled to rt and 3,4-difluorobenzonitrile (0.8 g, 5.75 mmol) was added. The solution was cooled further to −25° C. and methyl lithium/lithium bromide (1.5 M in diethyl ether, 9.59 ml, 14.38 mmol) was added slowly. The reaction was stirred at this temperature for 1 h and ammonium hydroxide solution (28% in water, 4.00 ml, 28.8 mmol) was added and the mixture was allowed to sit overnight at rt. The cerium salts were filtered off and washed with THF. The obtained THF solution was dried with MgSO4, filtered and concentrated. The product was diluted with ethyl ether and THF and HCl (4M in dioxane, 1.438 mL, 5.75 mmol) were added. The residue was concentrated, diluted with hexane and filtered affording the title compound.

1. customthe solution was purged
2. temperatureThe reaction was cooled to rt
3. temperatureThe solution was cooled further to −25° C.
4. waitto sit overnight at rt
5. filtrationThe cerium salts were filtered off
6. washwashed with THF
7. dry with materialThe obtained THF solution was dried with MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. additionwere added
11. concentrationThe residue was concentrated
12. additiondiluted with hexane
13. filtrationfiltered

ORD record

ord-8bed18835d2a47068361c03f3f0c9eaa

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278304B2