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

HRID 1453307노트

반응식

HRID 1453307 반응식
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]

참가 물질

6

반응물 2

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

생성물 1

HCID 26343860(2-Fluoro-4-methoxyphenyl)acetonitrile수율 75%

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 962Water용매2회HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c2cfc1580f7e4b11a5912e6e89070391
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473790B2

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