تفاعل #8600

معادلة التفاعل

4-chloro-2-picoline

ethyl 4-fluorobenzoate

lithium bis(trimethylsilyl)amide

→

2-(4-chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone

المردود 99.0%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىover 30 minutes
2. 2
   workup.ADDITIONUpon complete addition
3. 3
   أخرىthe cold bath was removed
4. 4
   تركيزThe reaction mixture was concentrated under reduced pressure and methanol
5. 5
   workup.ADDITIONwas added to the reaction
6. 6
   أخرىresulting in the formation of a white precipitate
7. 7
   ترشيحThe precipitate was collected by filtration
8. 8
   أخرىdried

الإجراء التجريبي

To a cold (0 ° C.) solution of 4-chloro-2-picoline (5.0 g,39 mmol) and ethyl 4-fluorobenzoate (6.6 g, 39 mmol) in tetrahydrofuran (100 mL) was added lithium bis(trimethylsilyl)amide (80 mL, 1.0 M in tetrahydrofuran, 80 mmol) dropwise via a pressure equalizing funnel over 30 minutes. Upon complete addition, the cold bath was removed and the resulting solution was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure and methanol was added to the reaction, resulting in the formation of a white precipitate. The precipitate was collected by filtration and dried to give 2-(4-chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone (9.6 g, 99%) as a white solid. 1H-NMR (DMSO-d6): δ 7.90 (m, 3H), 7.11 (t, 2H), 6.56 (s,1 H), 5.67 (s, 1 H), 4.14 (m, 2H); 19F-NMR (DMSO-d6): δ −115.67; MS m/z 250 (M+1).

المصدر