Cesium carbonate → 1,3-Dichloro-2-(trifluoromethyl)-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

HRID 1750801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1750801
[Cl:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:6]([Cl:9])[C:7]=1Br.Br[C:20]([C:22]([F:25])([F:24])[F:23])=[CH2:21].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:9][C:6]1[CH:5]=[C:4]([C:20]([C:22]([F:25])([F:24])[F:23])=[CH2:21])[CH:3]=[C:2]([Cl:1])[C:7]=1[C:22]([F:25])([F:24])[F:23]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 2726961-Propene, 2-bromo-3,3,3-trifluoro-HCID 534290842-(4-Bromo-3,5-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 866850511,3-Dichloro-2-(trifluoromethyl)-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneAusbeute 113,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 2-(3,5-dichloro-4-(bromo)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1 g, 2.86 mmol), 2-bromo-3,3,3-trifluoroprop-1-ene (0.60 g, 3.43 mmol), Cs2CO3 (2.86 mL, 2M, 5.72 mmol) and Pd(PPh3)2Cl2 (60 mg) in THF (30 mL) was heated at 70° C. in a sealed tube for 4 h. The mixture was cooled to rt and partitioned between ether and H2O. The aqueous layer was extracted with EA and the combined organic layers were dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by column chromatography over silica gel eluted with hexanes to give 1,3-dichloro-2-(trifluoromethyl)-5-(3,3,3-trifluoro-prop-1-en-2-yl)benzene (0.6 g; yield 66.7%) as colorless oil. 1H NMR (400 MHz, DMSO-d6): δ 7.72 (s, 2 H), 6.38 (s, 1 H), 6.28 (s, 1 H) ppm.

Aufarbeitung

  1. temperatureThe mixture was cooled to rt
  2. custompartitioned between ether and H2O
  3. extractionThe aqueous layer was extracted with EA
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customthe crude product was purified by column chromatography over silica gel
  7. washeluted with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-2ec062d024f149028ed481a431f49a68
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156860B2

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