Benzoic acid, 4-fluoro-, ethyl ester → 2-(4-Chloropyridin-2-yl)-1-(4-fluorophenyl)ethan-1-one

HRID 8504

반응식

HRID 8504 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[CH:3]=1.[F:9][C:10]1[CH:20]=[CH:19][C:13]([C:14](OCC)=[O:15])=[CH:12][CH:11]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][C:14]([C:13]2[CH:19]=[CH:20][C:10]([F:9])=[CH:11][CH:12]=2)=[O:15])[CH:3]=1

참가 물질

5

반응물 3

HCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 5813924-Chloro-2-methylpyridineHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 218740612-(4-Chloropyridin-2-yl)-1-(4-fluorophenyl)ethan-1-one수율 99%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  1. customover 30 minutes
  2. additionUpon complete addition
  3. customthe cold bath was removed
  4. concentrationThe reaction mixture was concentrated under reduced pressure and methanol
  5. additionwas added to the reaction
  6. customresulting in the formation of a white precipitate
  7. filtrationThe precipitate was collected by filtration
  8. customdried

출처 및 근거

ORD 기록
ord-94f2a48dfffc4dbe8606f31631f44660
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087618B2

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