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

HRID 336821ノート

反応式

HRID 336821 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-abe1ddc8f1d342d7844d0d488ce3bbcd
出典データセット
uspto-grants-2014_11
特許番号
US08889711B2

反応ノート

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