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Potassium Carbonate → 3,4-Dimethoxy-2-(2,2,2,-trifluoroethoxy)benzonitrile

HRID 2228521
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HRID 2228521 반응식
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[C:15]([O:16][CH3:17])=[C:14]([O:18][CH3:19])[CH:13]=[CH:12][C:9]=1[C:10]#[N:11].O([CH2:28][C:29]([F:32])([F:31])[F:30])S(C(F)(F)F)(=O)=O>CN(C)C=O.ClCCl>[CH3:17][O:16][C:15]1[C:8]([O:7][CH2:28][C:29]([F:32])([F:31])[F:30])=[C:9]([CH:12]=[CH:13][C:14]=1[O:18][CH3:19])[C:10]#[N:11]
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 119947582-Hydroxy-3,4-dimethoxybenzonitrile

생성물 1

HCID 184706363,4-Dimethoxy-2-(2,2,2,-trifluoroethoxy)benzonitrile수율 94.7%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 6344
Dichloromethane
용매

실험 절차

Potassium carbonate (6.91 g, 0.05 mol) was added to a stirred solution of 2-hydroxy-3,4-dimethoxybenzonitrile (from Example 10(c), 5.61 g, 0.031 mol) in dimethylformamide (30 ml). This was followed by the addition of a solution of 2,2,2-trifluoroethyl triflate (23.2 g, 0.10 mol). in dichloromethane (100 ml ) and the reaction was stirred at room temperature for 18 hours. The reaction was partitioned between 2N hydrochloric acid and ethyl acetate, the organic layer separated, washed sequentially with saturated aqueous brine and water, dried (MgSO4) and evaporated under reduced pressure. Trituration with diethyl ether followed by filtration afforded the subtitle compound as a colourless solid (7.67 g, 94%). Rf 0.76 (dichloromethane:methanol 95:5, v/v). MS m/z 279 (MNH4)+.

후처리

  1. customThe reaction was partitioned between 2N hydrochloric acid and ethyl acetate
  2. customthe organic layer separated
  3. washwashed sequentially with saturated aqueous brine and water
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. filtrationTrituration with diethyl ether followed by filtration

출처 및 근거

ORD 기록
ord-2168aaa6dd7c4f8ba59e5f6102d981fe
출처 데이터셋
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06417194B1

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