Thionyl Chloride → (2E)-3-(3-Fluorophenyl)-2-propenoyl chloride

HRID 1449392노트

반응식

HRID 1449392 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7](O)=[O:8].S(Cl)([Cl:15])=O>C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7]([Cl:15])=[O:8]

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 1551219(2E)-3-(3-Fluorophenyl)-2-propenoic acid

생성물 1

HCID 5706470(2E)-3-(3-Fluorophenyl)-2-propenoyl chloride수율 94.7%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

A mixture of trans 3-fluorocinnamic acid (32.3 g), thionyl chloride (48 g) and dry benzene (300 ml) was heated at reflux for 2 hours. Solvent and excess thionyl chloride were removed by distillation under reduced pressure leaving trans 3-fluorocinnamoyl chloride (34 g) as an oil. A solution of trans 3-fluorocinnamoy chloride (3.3 g) in dry toluene (100 ml) was added with stirring to a solution of cyclopropylamine (2.5 g) in dry ether (100 ml) at ambient temperature. The reaction mixture was heated at 30°-34° C. for 2 hours, and the solvent and excess amine were removed under reduced pressure. The residue was triturated with water, filtered and recrystallized from ethanol:water (1:10) to give trans 3-fluoro-N-cyclopropylcinnamamide (3.3 g), m. p. 90°-91° C.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customSolvent and excess thionyl chloride were removed by distillation under reduced pressure

출처 및 근거

ORD 기록
ord-bf52076d21344711a1285d53eb0261eb
출처 데이터셋
uspto-grants-1980_02
특허 번호
US04190674

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