Diethyl Ether → 2-(4-Chloro-2-methoxybenzoyl)cyclopropanecarbonitrile

HRID 561452

반응식

HRID 561452 반응식
BrC1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4]C=1OC.[Mg].[C:12]([CH:14]1[CH2:16][CH:15]1[C:17](N(OC)C)=[O:18])#[N:13].[CH2:23]([O:25][CH2:26][CH3:27])C>BrC(Br)C.C1COCC1.C(OCC)(=O)C>[Cl:8][C:6]1[CH:5]=[CH:4][C:27]([C:17]([CH:15]2[CH2:16][CH:14]2[C:12]#[N:13])=[O:18])=[C:26]([O:25][CH3:23])[CH:7]=1

참가 물질

8

반응물 4

HCID 3283Diethyl Ether2회HCID 5219352-Bromo-4-chloroanisoleHCID 5462224MagnesiumHCID 583925062-Cyano-N-methoxy-N-methylcyclopropanecarboxamide

생성물 1

HCID 583925482-(4-Chloro-2-methoxybenzoyl)cyclopropanecarbonitrile

시약·촉매·용매 3

HCID 112011,1-Dibromoethane촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 500 mg (2.26 mmol) of 2-bromo-4-chloroanisole in 5 ml of diethyl ether was added dropwise to 57.6 mg (2.37 mmol) of magnesium turnings in 10 ml of diethyl ether, activated by adding a few drops of dibromoethane, and the reaction mixture was heated under reflux overnight. The reaction solution was added dropwise under argon to a solution of 316 mg (2.05 mmol) of the compound from Example 73A in 10 ml of THF, and the reaction mixture was heated under reflux for 2 h. It was diluted with ethyl acetate, and the organic phase was washed with water and saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate 9/1) to result in 278 mg (58% of theory) of the title compound.

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for 2 h
  5. washthe organic phase was washed with water and saturated aqueous sodium bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate 9/1)

출처 및 근거

ORD 기록
ord-1a0de785186246ae8028054f82ac8333
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063234B2

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