Acetic Acid → 5-Fluoro-2-(3-fluoro-4-((E)-2-nitro-vinyl)phenoxymethyl)-pyridine

HRID 78079

반응식

HRID 78079 반응식
C(O)(=O)C.[F:5][C:6]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][N:17]=2)[CH:11]=[CH:10][C:7]=1[CH:8]=O.[N+:23]([CH3:26])([O-:25])=[O:24].C([O-])(=O)C.[NH4+]>C(OCC)(=O)C.O>[F:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][O:14][C:12]2[CH:11]=[CH:10][C:7](/[CH:8]=[CH:26]/[N+:23]([O-:25])=[O:24])=[C:6]([F:5])[CH:13]=2)=[N:17][CH:18]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 592553562-Fluoro-4-(5-fluoro-pyridin-2-ylmethoxy)benzaldehyde

생성물 1

HCID 592550775-Fluoro-2-(3-fluoro-4-((E)-2-nitro-vinyl)phenoxymethyl)-pyridine수율 94.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

To an acetic acid (20.0 mL) solution of 2-fluoro-4-(5-fluoro-pyridin-2-ylmethoxy)-benzaldehyde (901 mg, 3.62 mmol) described in Manufacturing Example 96-1-1 were added nitromethane (1.10 g, 18.1 mmol) and ammonium acetate (558 mg, 7.24 mmol) under nitrogen atmosphere, which was stirred for 2 hours at 110° C. Water and ethyl acetate were added to the reaction mixture, and the organic layer was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (1.00 g) as a crude product.

후처리

  1. extractionthe organic layer was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under a reduced pressure

출처 및 근거

ORD 기록
ord-5258d72a2f504e6bacb86bedab4c9dec
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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