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Sodium Hydroxide → 3-(4-(3-(Trifluoromethyl)phenoxy)phenyl)acrylonitrile

HRID 474601
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HRID 474601 반응식
[Br-].[C:2]([CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:3].[OH-].[Na+].[F:26][C:27]([F:44])([F:43])[C:28]1[CH:29]=[C:30]([CH:40]=[CH:41][CH:42]=1)[O:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=1>O.C(Cl)Cl>[F:26][C:27]([F:44])([F:43])[C:28]1[CH:29]=[C:30]([CH:40]=[CH:41][CH:42]=1)[O:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=[CH:4][C:2]#[N:3])=[CH:34][CH:33]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 11811037(Cyanomethyl)triphenylphosphonium bromideHCID 121487884-(3-(Trifluoromethyl)phenoxy)benzaldehyde

생성물 1

HCID 677761303-(4-(3-(Trifluoromethyl)phenoxy)phenyl)acrylonitrile수율 92%

시약·촉매·용매 2

HCID 962Water용매2회
HCID 6344
Dichloromethane
용매
2회

실험 절차

To a solution of (cyanomethyl)triphenylphosphonium bromide (8.61 g, 22.54 mmol) and NaOH (1.127 g, 28.2 mmol) in water (24 mL) and DCM (12 mL) was added 4-(3-(trifluoromethyl)phenoxy)benzaldehyde (5 g, 18.78 mmol) at 0° C. The mixture was stirred at room temperature for 4 h. DCM (50 mL) and water (50 mL) was added to the mixture, the organic phase was washed with water (50 mL), brine (50 mL), dried over anhydrous sodium sulfate and concentrated. Purification via flash chromatography afforded the title compound (5.07 g, 17.26 mmol, 92% yield) as pale yellow oil (slowly solidify to white solid). LCMS: rt=1.67 min, [M+H+]=290

후처리

  1. washthe organic phase was washed with water (50 mL), brine (50 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customPurification via flash chromatography

출처 및 근거

ORD 기록
ord-003e77e241f74e9f90b53704c42d9361
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08637536B2

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