4-Fluorobenzoyl chloride → (4-Fluorophenyl)[2-methoxy-5-(2,6-dimethyl-4-nitrophenoxy)phenyl]methanone

HRID 866009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 866009
[CH3:1][C:2]1[CH:3]=[C:4]([N+:18]([O-:20])=[O:19])[CH:5]=[C:6]([CH3:17])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([C:11]2[CH:10]=[C:9]([O:8][C:7]3[C:6]([CH3:17])=[CH:5][C:4]([N+:18]([O-:20])=[O:19])=[CH:3][C:2]=3[CH3:1])[CH:14]=[CH:13][C:12]=2[O:15][CH3:16])=[O:27])=[CH:24][CH:23]=1

Komponenten

5

Edukt 2

HCID 678794-Fluorobenzoyl chlorideHCID 100846724-(4-Methoxy-phenoxy)-3,5-dimethyl-nitrobenzene

Produkt 1

HCID 10046205(4-Fluorophenyl)[2-methoxy-5-(2,6-dimethyl-4-nitrophenoxy)phenyl]methanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4.5 g (16.5 mmol) of 3,5-dimethyl4-(4'-methoxyphenoxy)nitrobenzene and 6.63 g (41.8 mmol) of p-fluorobenzoyl chloride in 100 ml methylene chloride is added 15.8 g (83.3 mmol) of titanium tetrachloride. The reaction mixture is stirred for 8 days at room temperature, then poured into ice water (300 ml) and stirred 2 hours. The organic layer is separated, washed with 5% aqueous sodium carbonate, water, dried (CaSO4) and evaporated. The residue is triturated with ether-petroleum ether and recrystallized from methanol to give (4-fluorophenyl)[2-methoxy-5-(2,6-dimethyl-4-nitrophenoxy)phenyl]methanone, m.p. 167°-168°.

Aufarbeitung

  1. stirringstirred 2 hours
  2. customThe organic layer is separated
  3. washwashed with 5% aqueous sodium carbonate, water
  4. dry with materialdried (CaSO4)
  5. customevaporated
  6. customThe residue is triturated with ether-petroleum ether
  7. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-d3c72e7b887c4dc1a008f9f2a6d67eec
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05569674

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