1,2-Dibromoethane → 1-(4-Cyano-3-fluoro-phenyl)-cyclopropanecarboxylic acid methyl ester

HRID 1297580노트

반응식

HRID 1297580 반응식
[H-].[Na+].Br[CH2:4][CH2:5]Br.[CH3:7][O:8][C:9](=[O:20])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[C:13]([F:19])[CH:12]=1>O1CCCC1>[CH3:7][O:8][C:9]([C:10]1([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[C:13]([F:19])[CH:12]=2)[CH2:5][CH2:4]1)=[O:20]

참가 물질

5

반응물 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 58915197Methyl 2-(4-cyano-3-fluorophenyl)acetate

생성물 1

HCID 589151961-(4-Cyano-3-fluoro-phenyl)-cyclopropanecarboxylic acid methyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
75 °C

실험 절차

Sodium hydride (60% dispersion in mineral oil, 0.360 g) was suspended in anhydrous tetrahydrofuran (60 mL) under nitrogen. 1,2-Dibromoethane (2.0 mL) was added to the suspension, followed by (4-cyano-3-fluoro-phenyl)-acetic acid methyl ester (0.499 g). After the rate of gas evolution slowed, the reaction mixture was transferred to an oil bath and heated to 75° C. for 15 min. The reaction mixture was allowed to cool to ambient temperature and quenched with excess saturated ammonium chloride. The organic layer was separated and the remaining aqueous layer extracted with ethyl acetate (5×60 mL). The combined organics were dried with magnesium sulfate, filtered, and concentrated in vacuo. The crude product (0.637 g) was purified by silica gel chromatography (ethyl acetate:hexanes=2:3) yielding the title compound (0.500 g).

후처리

  1. customthe reaction mixture was transferred to an oil bath
  2. temperatureto cool to ambient temperature
  3. customquenched with excess saturated ammonium chloride
  4. customThe organic layer was separated
  5. extractionthe remaining aqueous layer extracted with ethyl acetate (5×60 mL)
  6. dry with materialThe combined organics were dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product (0.637 g) was purified by silica gel chromatography (ethyl acetate:hexanes=2:3)

출처 및 근거

ORD 기록
ord-386e510986b34d9db9ecd379dc1b43b6
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07250518B2

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