4-Fluorobenzoyl chloride → HCID 18424154, Verbindung

HRID 1585621Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1585621
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:15][N:16]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]1[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>ClCCCl>[CH3:15][N:16]1[C:20]([C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)=[C:19]([CH3:21])[CH:18]=[C:17]1[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

Komponenten

5

Edukt 3

HCID 678794-Fluorobenzoyl chlorideHCID 118467Ethyl 1,4-dimethyl-1H-pyrrole-2-acetateHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 18424154HCID 18424154, VerbindungAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Versuchsvorschrift

A solution of 3.95 g. (0.025 mole) of p-fluorobenzoyl chloride and 3.32 g. (0.025 mole) of aluminum chloride in 20 ml. of 1,2-dichloroethane is added dropwise to a solution of 4.52 g. (0.025 mole) of ethyl 1,4-dimethylpyrrole-2-acetate in 20 ml. of 1,2-dichloroethane at room temperature. The reaction mixture is stirred for 2 hours, and then cooled and poured into ice-dilute HCl. The organic phase is separated and washed successively with N,N-dimethyl-1,3-propanediamine, dilute hydrochloric acid and a saturated solution of sodium chloride; dried over anhydrous magnesium sulfate; and the solvent evaporated. The residuc is triturated with hot hexane and crystals form upon cooling. There is obtained about 1.9 g. (25% yield) of ethyl 1,4-dimethyl-5-(p-fluorobenzoyl)-pyrrole-2-acetate as a white solid, m.p. 84-86° C. Upon recrystallization from methanol, the m.p. is 87-89° C.

Aufarbeitung

  1. customat room temperature
  2. temperaturecooled
  3. additionpoured into ice-dilute HCl
  4. customThe organic phase is separated
  5. washwashed successively with N,N-dimethyl-1,3-propanediamine, dilute hydrochloric acid
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customand the solvent evaporated
  8. customThe residuc is triturated with hot hexane and crystals
  9. customform
  10. temperatureupon cooling
  11. customThere is obtained about 1.9 g

Quellen und Nachweise

ORD-Eintrag
ord-caabbd02b6fe45dfb56d590aef7ad990
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05939417

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