Reaktion #220442

Reaktionsgleichung

HCl

tert-butyllithium

3-bromofluorobenzene

THF

anthranilonitrile

THF

→

2-Amino-3′-fluorobenzophenone

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedid not rise above −74° C
2. 2
   TemperaturThe reaction was warmed to 0° C.
3. 3
   workup.STIRRINGstirred for 2 hours
4. 4
   workup.STIRRINGstirring
5. 5
   workup.WAITcontinued for 30 minutes
6. 6
   Sonstigethe layers were separated
7. 7
   ExtraktionThe aqueous layer was back-extracted thrice with ethyl acetate
8. 8
   WaschenThe combined extracts were washed with brine
9. 9
   Trocknendried over Na2SO4
10. 10
    Filtrationfiltered
11. 11
    Einengenconcentrated
12. 12
    SonstigeThe residue was purified via HPLC
13. 13
    Wascheneluting with 93:7 hexanes/ethyl acetate

Vorschrift

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.

Quelle