Hydrochloric Acid → (2-Aminophenyl)(3-fluorophenyl)methanone

Temperature

-78 °C

A solution of 3-bromofluorobenzene (1 eq.) in THF was cooled to −78° C. under nitrogen and treated with tert-butyllithium (2.05 eq., 1.6 M solution in pentane) at a rate of 40 mL/h. The internal temperature did not rise above −74° C. The orange solution was stirred at −78° C. for 30 minutes prior to the addition of anthranilonitrile (0.6 eq.) as a solution in THF. The reaction was warmed to 0° C. and stirred for 2 hours. 3N HCl was added to the mixture and stirring continued for 30. minutes. The reaction was diluted with ethyl acetate and the layers were separated. The aqueous layer was back-extracted thrice with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified via HPLC eluting with 93:7 hexanes/ethyl acetate.

1. customdid not rise above −74° C
2. temperatureThe reaction was warmed to 0° C.
3. stirringstirred for 2 hours
4. stirringstirring
5. customthe layers were separated
6. extractionThe aqueous layer was back-extracted thrice with ethyl acetate
7. washThe combined extracts were washed with brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was purified via HPLC
12. washeluting with 93:7 hexanes/ethyl acetate

ORD record

ord-3f40bd33b1af4279ae14730390b12989

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06696438B2