Pyridine → 2-Fluoro-4-formylbenzonitrile

HRID 379060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 379060
[F:1][C:2]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(N(CC)CC)C.N1C=CC=CC=1>C(Cl)Cl.CS(C)=O>[F:1][C:2]1[CH:9]=[C:8]([CH:10]=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 8471TriethylamineHCID 118296312-Fluoro-4-(hydroxymethyl)benzonitrile

Produkt 1

HCID 112173392-Fluoro-4-formylbenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Fluoro-4-hydroxymethylbenzonitrile (Example 9, Step C) 10 g, 0,066 mol) and triethylamine (32.3 mL, 0.231 mol) were dissolved in CH2Cl2 (100 mL)-DMSO (20 mL) at <5° C. with stirring and treated dropwise with a solution of pyridine.SO3 complex (31.5 g, 0.198 mol) in DMSO (70 mL) maintaining the reaction mixture temperature at <10° C. The reaction mixture was stirred at 5° C. for 1 hr after the addition, then at 20° C. for 1 hr, then partitioned between CH2Cl2 and H2O. The organic layer was separated, washed well with H2O, brine, and dried (Na2SO4). Filtration and concentration gave the title compound after purification by chromatography (silica gel, hexane: EtOAc, 3:1). 1H NMR (CDCl3) δ 10.06 (d, 1H, J=2 Hz), 7.86 (dd, 1H, J=5, 8 Hz), 7.798 (dd, 1H, J=1, 8 Hz), 7.728 (dd, 1H, J=1, 8 Hz).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at 5° C. for 1 hr
  2. additionafter the addition
  3. custompartitioned between CH2Cl2 and H2O
  4. customThe organic layer was separated
  5. washwashed well with H2O, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationFiltration and concentration

Quellen und Nachweise

ORD-Eintrag
ord-a5c2456b8b50434daf4a0b33e4af95b7
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06297239B1

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