Cesium carbonate → HCID 57633709, 화합물

HRID 2240876노트

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HRID 2240876 반응식
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:21][CH2:22][F:23]>C(#N)C>[F:23][CH2:22][CH2:21][NH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:11])([F:12])[F:13])[CH:3]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 129822-Fluoroethyl bromide2회HCID 5221704-Amino-2-(trifluoromethyl)benzonitrile

생성물 1

HCID 57633709HCID 57633709, 화합물수율 79.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
120 °C

실험 절차

To a solution of 4-amino-2-(trifluoromethyl)benzonitrile (0.100 g, 0.54 mmol) in acetonitrile (3 mL) was added cesium carbonate (0.438 g, 1.34 mmol) and 1-bromo-2-fluoroethane (0.340 g, 2.68 mmol). The mixture was heated in a microwave at 120° C. for 15 min. Upon cooling, additional 1-bromo-2-fluoroethane (0.340 g, 2.68 mmol) was added and the reaction was heated in the microwave at 140° C. for 20 min. Upon cooling, the solids were filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo and the residue was purified by radial chromatography (10-40% ethyl acetate-hexane gradient) to give 0.100 g of a mixture (6:1) of the title compound and 4-[bis(2-fluoroethyl)amino]-2-(trifluoromethyl)benzonitrile as a white solid, which was used as such in the next reaction.

후처리

  1. temperatureUpon cooling
  2. temperaturethe reaction was heated in the microwave at 140° C. for 20 min
  3. temperatureUpon cooling
  4. filtrationthe solids were filtered off
  5. washwashed with ethyl acetate
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by radial chromatography (10-40% ethyl acetate-hexane gradient)

출처 및 근거

ORD 기록
ord-90416fac95e74e16af449b2d5c69ff5e
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723385B2

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