Ammonium Chloride → (2,5-Dichloropyridin-3-yl)(2-fluoro-3-methoxy-6-vinylphenyl)methanol

HRID 1987142노트

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HRID 1987142 반응식
[Li]CCCC.Br[C:7]1[C:8]([Cl:14])=[N:9][CH:10]=[C:11]([Cl:13])[CH:12]=1.[F:15][C:16]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]([CH:26]=[CH2:27])[C:17]=1[CH:18]=[O:19].[NH4+].[Cl-]>C(OC(C)C)(C)C.C1C=CC=CC=1>[Cl:14][C:8]1[C:7]([CH:18]([C:17]2[C:20]([CH:26]=[CH2:27])=[CH:21][CH:22]=[C:23]([O:24][CH3:25])[C:16]=2[F:15])[OH:19])=[CH:12][C:11]([Cl:13])=[CH:10][N:9]=1

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 129015963-Bromo-2,5-dichloropyridineHCID 577227732-Fluoro-3-methoxy-6-vinylbenzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 86609785(2,5-Dichloropyridin-3-yl)(2-fluoro-3-methoxy-6-vinylphenyl)methanol

시약·촉매·용매 2

HCID 241Benzene용매HCID 7914Diisopropyl Ether용매3회

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온도
-78 °C

실험 절차

To a stirred solution of nBuLi (1.6 M in hexane, 29.0 mL, 46.4 mmol) in diisopropyl ether (80 mL) was added 3-bromo-2,5-dichloropyridine (10.5 g, 46.4 mmol) in diisopropylether (60 mL) slowly at −78° C. The resulting suspension was treated with 2-fluoro-3-methoxy-6-vinylbenzaldehyde (7.6 g, 42.2 mmol) in diisopropylether (60 mL) and benzene (3 mL), and allowed to stir at −78° C. for 30 min followed by warming to room temperature as the bath did. The mixture was treated with saturated NH4Cl solution and extracted with EtOAc (×3). The combined organics were washed with brine, dried (Na2SO4), concentrated, and purified by flash chromatography to afford the title compound.

후처리

  1. temperatureby warming to room temperature as the bath
  2. extractionextracted with EtOAc (×3)
  3. washThe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-006c1b9c4aad460b908701196ca4ad03
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550478B2

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