Triethylamine → Methyl 3-(2-bromo-3,5-difluorophenyl)propanoate

HRID 625696

Reaktionsgleichung

Reaktionsgleichung von HRID 625696
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[Br:10].[CH3:11][O:12][CH:13]([O:16]C)[CH:14]=[CH2:15].C(N(CC)CC)C>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[Br:10][C:3]1[C:4]([F:9])=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[CH2:15][CH2:14][C:13]([O:12][CH3:11])=[O:16]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 80145Acrolein dimethyl acetalHCID 27245171,2-Dibromo-3,5-difluorobenzene

Produkt 1

HCID 89826041Methyl 3-(2-bromo-3,5-difluorophenyl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 1,2-dibromo-3,5-difluorobenzene (4.5 g), 3,3-dimethoxyprop-1-ene (5.1 mL), tetrabutylammonium chloride (4.6 g) and triethylamine (3.5 mL) in N,N-dimethylformamide (50 mL) is purged with nitrogen for 20 minutes. Palladium-(II)-acetate (111 mg) is added and the mixture heated for 16 hours at 90° C. After cooling the mixture is partitioned between aqueous HCl (1 M) and diethyl ether, the organic layer dried (Na2SO4), volatiles evaporated under reduced pressure and the residue purified by column chromatography (silica gel; hexane:ethyl acetate 98:2→80:20) to give the title compound (Yield 3.6 g).

Aufarbeitung

  1. customis purged with nitrogen for 20 minutes
  2. additionPalladium-(II)-acetate (111 mg) is added
  3. temperatureAfter cooling the mixture
  4. customis partitioned between aqueous HCl (1 M) and diethyl ether
  5. dry with materialthe organic layer dried (Na2SO4)
  6. customvolatiles evaporated under reduced pressure
  7. customthe residue purified by column chromatography (silica gel; hexane:ethyl acetate 98:2→80:20)

Quellen und Nachweise

ORD-Eintrag
ord-8f53b8bc5e954936a05f94d1a5e40149
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09308194B2

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