Ammonium → 3,4-Diethoxy-2-fluorobenzonitrile

HRID 244331노트

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HRID 244331 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH3:10])=[C:4]([O:11][CH2:12][CH3:13])[C:3]=1[F:14].[Cu][C:16]#[N:17].C(OCC)(=O)C.[NH4+]>CN(C)C=O>[CH2:12]([O:11][C:4]1[C:3]([F:14])=[C:2]([CH:7]=[CH:6][C:5]=1[O:8][CH2:9][CH3:10])[C:16]#[N:17])[CH3:13]

참가 물질

6

반응물 4

HCID 223AmmoniumHCID 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

To a solution of 1-bromo-3,4-diethoxy-2-fluorobenzene (12.0 g, 45.6 mmoL) in N,N-dimethylformamide (DMF) (60 mL), copper (I) cyanide (6.8 g, 68.3 mmoL) was added at room temperature and then stirred at 155° C. for 3 hours. After ice cooling the reaction solution, ethyl acetate and 28% aqueous ammonium were added thereto to separate the organic layer. This organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated. The residue was purified by silica gel column chromatography (n-hexane, ethyl acetate) to give 9.0 g of the captioned compound (yield: 94.3%).

후처리

  1. customto separate the organic layer
  2. washThis organic layer was washed with water and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel column chromatography (n-hexane, ethyl acetate)

출처 및 근거

ORD 기록
ord-003d9528fd9c4406a0f00237c8a9d5b2
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658620B2

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