Cesium carbonate → HCID 86697028, Verbindung

HRID 536175Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 536175
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([C:10]([F:13])([F:12])[F:11])[CH:4]=1.[B-](F)(F)(F)[C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][CH:16]=1.[K+].C([O-])([O-])=O.[Cs+].[Cs+]>COC1CCCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Cl:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:15]2[CH:20]=[CH:19][C:18]([CH:21]=[O:22])=[CH:17][CH:16]=2)=[CH:4][C:5]=1[C:10]([F:13])([F:12])[F:11]

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 27781144-Chloro-3-(trifluoromethyl)benzyl bromideHCID 23697319Potassium 4-formylphenyltrifluoroborate

Produkt 1

HCID 86697028HCID 86697028, VerbindungAusbeute 51,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 138539Cyclopentyl methyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of 4-(bromomethyl)-1-chloro-2-(trifluoromethyl)benzene (4.5 g, 16.45 mmol), potassium trifluoro(4-formylphenyl)borate (3.52 g, 16.62 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.672 g, 0.823 mmol) and Cs2CO3 (16.08 g, 49.4 mmol) in cyclopentyl methyl ether (100 mL) and water (100 mL). The mixture was charged with Argon and stirred for overnight at 80° C. The result mixture was cooled to room temperature and partitioned with water 100 mL and ethyl acetate 100 mL. The organic phase was washed by water, brine and dried over sodium sulfate, the solvent was removed and the residue was purified via flash column chromatography. Removed the solvent afforded the title compound (2.55 g). LC-MS (ESI): m/z 299 [M+H]+

Aufarbeitung

  1. additionThe mixture was charged with Argon
  2. temperatureThe result mixture was cooled to room temperature
  3. custompartitioned with water 100 mL and ethyl acetate 100 mL
  4. washThe organic phase was washed by water, brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed
  7. customthe residue was purified via flash column chromatography
  8. customRemoved the solvent

Quellen und Nachweise

ORD-Eintrag
ord-881d5b2c67b74d76915324d994e800fa
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859573B2

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