Triphenylphosphine → 1-(3-Bromo-4-{[(4-chloro-2-pyridinyl)methyl]oxy}phenyl)ethanone

HRID 63272

Reaktionsgleichung

Reaktionsgleichung von HRID 63272
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][OH:9])[CH:3]=1.[Br:10][C:11]1[CH:12]=[C:13]([C:18](=[O:20])[CH3:19])[CH:14]=[CH:15][C:16]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:10][C:11]1[CH:12]=[C:13]([C:18](=[O:20])[CH3:19])[CH:14]=[CH:15][C:16]=1[O:9][CH2:8][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][N:5]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 6080941-(3-Bromo-4-hydroxyphenyl)ethanoneHCID 2763167(4-Chloropyridin-2-yl)methanolHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 682019601-(3-Bromo-4-{[(4-chloro-2-pyridinyl)methyl]oxy}phenyl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of (4-chloro-2-pyridinyl)methanol (Commercial eg Aldrich) (0.2 g) in THF (5 ml) were added 1-(3-bromo-4-hydroxyphenyl)ethanone (0.3 g) and triphenylphosphine (0.547 g). This was stirred for 10 min before cooling and adding slowly DEAD (0.363 g). This was stirred for 16 h. The reaction mixture was partitioned between water and ethyl acetate. The aqueous was reextracted with ethyl acetate and the combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo. This was purified through silica eluting with 0-35% ethyl acetate in hexane to give the title compound, 0.30 g

Aufarbeitung

  1. temperaturebefore cooling
  2. stirringThis was stirred for 16 h
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. washthe combined organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThis was purified through silica eluting with 0-35% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-a429b1da3344417d94b8f0ecf4efed2d
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447074B2

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