4-Chlorobutyronitrile → 4-(7-bromo-1H-indol-3-yl)butanenitrile

HRID 12623

반응식

HRID 12623 반응식
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.Cl[CH2:12][CH2:13][CH2:14][C:15]#[N:16].C([Mg]Br)C.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH2:12][CH2:13][CH2:14][C:15]#[N:16]

참가 물질

6

반응물 4

HCID 123364-ChlorobutyronitrileHCID 25517Ammonium ChlorideHCID 27570207-BromoindoleHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 686933874-(7-bromo-1H-indol-3-yl)butanenitrile

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To an anhydrous toluene (12 mL) solution of 7-bromoindole (1.0 g) and 4-chlorobutyronitrile (0.26 g), ethylmagnesium bromide (3.0M diethyl ether solution; 1.7 mL) was added dropwise under ice cooling and the mixture was heated to reflux for 4.5 hours. To the reaction mixture, an aqueous saturated ammonium chloride solution was added under ice cooling, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and saturated saline, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10→70:30) to obtain the titled compound having the following physical properties (0.40 g).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4.5 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed in turn with water and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10→70:30)

출처 및 근거

ORD 기록
ord-27fdefc4bc05481e8d695825b2e4ecdb
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728023B2

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