Oxalyl chloride → 8-Fluoro-2,3-dihydro-4H-1-benzopyran-4-one

HRID 600421Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600421
C(Cl)(=O)C(Cl)=O.[F:7][C:8]1[CH:19]=[CH:18][CH:17]=[CH:16][C:9]=1[O:10][CH2:11][CH2:12][C:13]([OH:15])=O.[Cl-].[Al+3].[Cl-].[Cl-]>CN(C=O)C.C(Cl)Cl>[F:7][C:8]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:9]=1[O:10][CH2:11][CH2:12][C:13]2=[O:15]

Komponenten

6

Edukt 3

HCID 65578Oxalyl chlorideHCID 15457213-(2-fluorophenoxy)propanoic AcidHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 139538178-Fluoro-2,3-dihydro-4H-1-benzopyran-4-oneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Oxalyl chloride (8.79 mL) and one drop of DMF were added to an ice cold solution of 3-(2-fluorophenoxy)propanoic acid (9.27 g) in methylene chloride (50 mL). The solution was stirred at 0° C. for two hours, aluminum chloride (7.39 g, 55.42 mM) was added and the solution was stirred for 16 hours at room temperature. The mixture was poured onto ice water, and extracted three times with methylene chloride. The combined organics were washed with 0.5M NaOH and brine, dried, evaporated, and purified by column chromatography (eluting with 20% EtOAc/Hex) to give 8-fluorochroman-4-one (3) (8.20 g, 98%).

Aufarbeitung

  1. stirringthe solution was stirred for 16 hours at room temperature
  2. additionThe mixture was poured onto ice water
  3. extractionextracted three times with methylene chloride
  4. washThe combined organics were washed with 0.5M NaOH and brine
  5. customdried
  6. customevaporated
  7. custompurified by column chromatography (eluting with 20% EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-f0e520929165432c8e283d547cb1f46f
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902187B2

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