반응 #9358

반응 방정식

t-butyl nitrite

amine

8-amino-3,4-dihydro-2H-naphthalen-1-one

BF3.OEt2

→

8-fluoro-3,4-dihydro-2H-naphthalen-1-one

용매

CH2Cl2

pentane

CH2Cl2

CH2Cl2

반응 조건

후처리

1. 1
   여과filtered
2. 2
   기타the solids were collected
3. 3
   세척washed with ether
4. 4
   기타dried under vacuum
5. 5
   기타The solids were placed in a flask
6. 6
   온도heated to 115° C. for 10–15 min.
7. 7
   workup.ADDITIONfollowed by addition of 2N NaOH and CHCl3
8. 8
   여과The suspension was filtered
9. 9
   추출the aqueous phase was extracted with CHCl3
10. 10
    건조dried over MgSO4
11. 11
    여과filtered
12. 12
    기타purified by chromatography on SiO2 with 15% EtOAc

실험 절차

The amine (Intermediate J3, 1.83 g, 11.3 mmol) in CH2Cl2 (17 mL) was added to BF3.OEt2 (2.80 mL, 22.1 mmol) at −15° C. More CH2Cl2 (20 mL) was added to the precipitate. Next, t-butyl nitrite (1.8 mL, 12.9 mmol) in CH2Cl2 (20 mL) was added at −15° C. and stirred for 10 min. and at 0° C. for 20 m. The mixture was diluted with pentane (40 mL), filtered and the solids were collected, washed with ether, and dried under vacuum. The solids were placed in a flask and heated to 115° C. for 10–15 min. followed by addition of 2N NaOH and CHCl3. The suspension was filtered and the aqueous phase was extracted with CHCl3. The organic layers were combined, dried over MgSO4, filtered and purified by chromatography on SiO2 with 15% EtOAc:Hx. The product, 8-fluoro-3,4-dihydro-2H-naphthalen-1-one (Intermediate J4) was isolated; 750 mg (40%).

출처