Potassium Cyanide → (2-Fluoro-4-methoxyphenyl)acetonitrile

HRID 1453307ノート

反応式

HRID 1453307 の反応式
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[F:11].[C-:12]#[N:13].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[F:11][C:4]1[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=1[CH2:2][C:12]#[N:13]

参加物

6

反応物 2

HCID 9032Potassium CyanideHCID 109550331-(Bromomethyl)-2-fluoro-4-methoxybenzene

生成物 1

HCID 26343860(2-Fluoro-4-methoxyphenyl)acetonitrile収率 75%

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 1-Bromomethyl-2-fluoro-4-methoxy-benzene (4.5 g, 21 mmol) and Tetrabutylammonium iodide (0.66 g, 2.1 mmol) in CH2Cl2 (50 mL) was added a solution potassium cyanide (4.0 g, 60 mmol) in water (50 mL). The resulting biphasic mixture was stirred vigorously for 8 hours. The reaction was poured into water (100 mL) and extracted with CH2Cl2 (2×50 mL). The organics were washed with water (100 mL) and brine (100 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (10-30% EtOAc in hexanes) to give the product (2.6 g, 75% yield) as a clear oil. 1H NMR (300 MHz, CDCl3) δ: 3.66 (s, 2H), 3.82 (s, 3H), 6.69 (m, 2H), 7.31 (m, 1H).

後処理

  1. extractionextracted with CH2Cl2 (2×50 mL)
  2. washThe organics were washed with water (100 mL) and brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (10-30% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-c2cfc1580f7e4b11a5912e6e89070391
出典データセット
uspto-grants-2009_01
特許番号
US07473790B2

反応ノート

読み込み中…