Ammonia → 3,4-Diethoxy-2-fluorobenzonitrile

HRID 2223755노트

반응식

HRID 2223755 반응식
[Cu][C:2]#[N:3].Br[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH3:13])=[C:7]([O:14][CH2:15][CH3:16])[C:6]=1[F:17].C(OCC)(=O)C.N>CN(C)C=O>[CH2:15]([O:14][C:7]1[C:6]([F:17])=[C:5]([CH:10]=[CH:9][C:8]=1[O:11][CH2:12][CH3:13])[C:2]#[N:3])[CH3:16]

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 230937081-Bromo-3,4-diethoxy-2-fluorobenzeneHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 230937173,4-Diethoxy-2-fluorobenzonitrile수율 94.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
155 °C

실험 절차

Copper(I)cyanide (6.8 g, 68.3 mmol) was added to a solution of 1-bromo-3,4-diethoxy-2-fluorobenzene (12.0 g, 45.6 mmol) in N,N-dimethylformamide (DMF) (60 mL) at room temperature, and this was then stirred at 155° C. for 3 hours. The reaction solution was cooled on ice. Following addition of ethyl acetate and 28% aqueous ammonia, the organic layer was separated and washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was removed after filtration, and the residue was purified by silica gel column chromatography (n-hexane, ethyl acetate) to give 9.0 g of the subject compound (yield: 94.3%).

후처리

  1. temperatureThe reaction solution was cooled on ice
  2. customthe organic layer was separated
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed
  6. filtrationafter filtration
  7. customthe residue was purified by silica gel column chromatography (n-hexane, ethyl acetate)

출처 및 근거

ORD 기록
ord-658744872cee4cc89b01c6b862acc909
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07375236B2

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