반응 #1447100

반응 방정식

KOtBu

ethyl (4-ethyl-phenyl)-acetate

1-bromo-4-cyano-3,5-difluoro-benzene

hydrochloric acid

sodium hydroxide

→

1-Bromo-4-cyano-3-methoxy-5-(4-ethyl-benzyl)-benzene

용매

NMP

NMP

methanol

반응 조건

후처리

1. 1
   workup.ADDITIONcharged with a stir bar
2. 2
   기타maintains below 10° C
3. 3
   workup.STIRRINGthe resulting mixture is stirred overnight at 100° C
4. 4
   workup.STIRRINGthe mixture is stirred for another h at 100° C
5. 5
   기타The methanol fraction is evaporated
6. 6
   workup.ADDITIONwater (200 mL) is added to the residue
7. 7
   추출the resulting mixture is extracted with ethyl acetate
8. 8
   세척The combined organic extracts are washed twice with water, twice with brine
9. 9
   건조dried (MgSO4)
10. 10
    기타The solvent is evaporated
11. 11
    세척the residue is washed with methanol
12. 12
    기타The insoluble residue is separated by filtration
13. 13
    기타dried
14. 14
    기타to give the white product

실험 절차

KOtBu (11.8 g) is added to a flask charged with a stir bar and dry NMP (40 mL) and chilled to −10° C. under argon atmosphere. A solution of ethyl (4-ethyl-phenyl)-acetate (10.1 g) and 1-bromo-4-cyano-3,5-difluoro-benzene (11.5 g) in NMP (40 mL) is added at such a rate that the reaction temperature maintains below 10° C. After stirring for 1 hour at room temperature, methanol (50 mL) and 1 M aqueous sodium hydroxide solution (39 mL) are added and the resulting mixture is stirred overnight at 100° C. Then, 4 M aqueous hydrochloric acid (100 mL) is added and the mixture is stirred for another h at 100° C. The methanol fraction is evaporated, water (200 mL) is added to the residue and the resulting mixture is extracted with ethyl acetate. The combined organic extracts are washed twice with water, twice with brine and dried (MgSO4). The solvent is evaporated and the residue is washed with methanol. The insoluble residue is separated by filtration and dried to give the white product.

출처