反応 #1447100

反応方程式

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

溶媒

NMP

NMP

methanol

反応条件

後処理

1. 1
   workup.ADDITIONcharged with a stir bar
2. 2
   その他maintains 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
   その他The methanol fraction is evaporated
6. 6
   workup.ADDITIONwater (200 mL) is added to the residue
7. 7
   抽出the resulting mixture is extracted with ethyl acetate
8. 8
   洗浄The combined organic extracts are washed twice with water, twice with brine
9. 9
   乾燥dried (MgSO4)
10. 10
    その他The solvent is evaporated
11. 11
    洗浄the residue is washed with methanol
12. 12
    その他The insoluble residue is separated by filtration
13. 13
    その他dried
14. 14
    その他to give the white product

実験手順

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.

出典