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3-Iodobenzonitrile → 3-{1-[1-(4-Chlorophenyl)cyclobutyl]-2-nitroethyl}benzonitrile

HRID 331691
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HRID 331691 반응식
I[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].C([Mg]Cl)(C)C.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2(/[CH:26]=[CH:27]/[N+:28]([O-:30])=[O:29])[CH2:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1>O1CCCC1>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2([CH:26]([C:2]3[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=3)[C:5]#[N:6])[CH2:27][N+:28]([O-:30])=[O:29])[CH2:23][CH2:24][CH2:25]2)=[CH:20][CH:21]=1
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참가 물질

5

반응물 3

HCID 1443413-IodobenzonitrileHCID 667468521-Chloro-4-{1-[(E)-2-nitroethenyl]cyclobutyl}benzeneHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 667475753-{1-[1-(4-Chlorophenyl)cyclobutyl]-2-nitroethyl}benzonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

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온도
-30 °C

실험 절차

3-Iodobenzonitrile (3.76 g, 16.41 mmol) dissolved in tetrahydrofuran (1.5 ml) was cooled to −30° C. A solution of isopropylmagnesium chloride in tetrahydrofuran (2 M, 8.84 ml, 17.67 mmol) was added dropwise at −30° C. over 25 min. The reaction mixture was cooled to −78° C. A solution of (E)-1-chloro-4(1-(2-nitrovinyl)cyclobutyl)benzene (3.0 g, 12.62 mmol) in tetrahydrofuran (0.5 ml) was added dropwise. Aqueous work-up yielded the desired product which was used without further purification for the next step. Yield: 3.3 g (8.71 mmol, 69%, purity: 90% by HPLC)

후처리

  1. temperatureThe reaction mixture was cooled to −78° C

출처 및 근거

ORD 기록
ord-6f6116da9c62469bae9305d10c9e8dcb
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08877794B2

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