Hydrochloric Acid → 3-(2-Fluoro-4-methoxyphenyl)-3-oxopropanenitrile

HRID 336821노트

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HRID 336821 반응식
[C:1](#[N:3])[CH3:2].[Li+].CCC[CH2-].[F:9][C:10]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:11]=1[C:12](OC)=[O:13].Cl>O1CCCC1>[F:9][C:10]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:11]=1[C:12](=[O:13])[CH2:2][C:1]#[N:3]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 61028n-Butyl lithiumHCID 21255685Methyl 2-fluoro-4-methoxybenzoate

생성물 1

HCID 534039523-(2-Fluoro-4-methoxyphenyl)-3-oxopropanenitrile수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

To a solution of 4.4 g (108.6 mmol, 5.7 ml) of acetonitrile diluted in 50 ml of anhydrous tetrahydrofuran are added dropwise at −78° C. under argon 27.1 ml of a N-butyllithium solution (2.5M in hexane, 67.8 mmol), the reaction mixture is stirred 30 min at −78° C., then 5 g (27.15 mmol) of methyl 2-fluoro-4-methoxybenzoate diluted in 30 ml of tetrahydrofuran are added dropwise at −78° C. to the reaction mixture. This mixture is stirred 2 h at −78° C., then a 1M hydrochloric acid solution is added, and the product is extracted several times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate and concentrated. The solid is triturated in 15 ml of methanol to yield 4.4 g (84%) of 3-(2-fluoro-4-methoxyphenyl)-3-oxopropanenitrile in beige solid form.

후처리

  1. additionare added dropwise at −78° C. to the reaction mixture
  2. stirringThis mixture is stirred 2 h at −78° C.
  3. extractionthe product is extracted several times with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe solid is triturated in 15 ml of methanol

출처 및 근거

ORD 기록
ord-abe1ddc8f1d342d7844d0d488ce3bbcd
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889711B2

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