Sodium Iodide → Benzene, 4-bromo-2-[(4,4-difluoro-3-buten-1-yl)oxy]-1-fluoro-

HRID 30593

Reaktionsgleichung

Reaktionsgleichung von HRID 30593
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:19][CH2:20][CH:21]=[C:22]([F:24])[F:23]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(C(C)=O)C.ClCCl>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:9][CH2:19][CH2:20][CH:21]=[C:22]([F:24])[F:23])[CH:4]=1

Komponenten

8

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 183421Phenol, 5-bromo-2-fluoro-HCID 27822404-Bromo-1,1-difluorobut-1-ene

Produkt 1

HCID 59790300Benzene, 4-bromo-2-[(4,4-difluoro-3-buten-1-yl)oxy]-1-fluoro-Ausbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 21218Trioctylmethylammonium chlorideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 2-fluoro-5-bromophenol (2.40 g), potassium carbonate (2.31 m), Aliquat 336 (5 drops), sodium iodide (catalytic) and 4-bromo-1,1-difluoro-1-butene (1.79 mL) in methyl ethyl ketone was placed in a pressure vessel and heated in a 82° oil bath for 15 hours. The reaction mixture was cooled, diluted with dichloromethane, filtered and evaporated in vacuo. The resultant residue was purified by flash chromatography (silica gel, eluant: 2.5% ethyl acetate/hexane to afford 4-bromo-2-(4,4-difluorobut-3-enyloxy)-1-fluorobenzene, 2.23 g (63% yield), identified by NMR analysis.

Aufarbeitung

  1. customwas placed in a pressure vessel
  2. temperatureheated in a 82° oil bath for 15 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe resultant residue was purified by flash chromatography (silica gel, eluant

Quellen und Nachweise

ORD-Eintrag
ord-64e03f43ee504125a8fbde98ebe10950
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423158B2

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