Benzene, 1-bromo-2-(trifluoromethyl)- → HCID 9899486, Verbindung

HRID 1591502Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1591502
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([Sn](C)(C)C)=[CH:4][CH:3]=1.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([F:22])([F:21])[F:20]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:20][C:19]([F:22])([F:21])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1

Komponenten

5

Edukt 2

HCID 9806Benzene, 1-bromo-2-(trifluoromethyl)-HCID 617834Stannane, trimethyl(4-methylphenyl)-

Produkt 1

HCID 9899486HCID 9899486, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 388 mg (1.52 mmol,1.4 eq.) of 4-methylphenyltrimethylstannane (Example 69, Step A) in 5 mL of toluene under a nitrogen atmosphere was treated with 238 mg of 2-bromobenzotrifluoride (1.06 mmol) and 64 mg of tetrakis(triphenylphosphine) palladium(0) and the resulting solution heated at reflux for 14 hours. The mixture was cooled, filtered and concentrated under vacuum to give an amber oil that was chromatographed on silica, eluting with hexane, to give the product. 1H NMR (300 MHz,CDCl3): 2.41 (s,3H), 7.2-7.8 (m,8H). EI-MS: calculated for C14H11F3 236; found 236 (M+,100%).

Aufarbeitung

  1. temperaturethe resulting solution heated
  2. temperatureat reflux for 14 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give an amber oil that
  7. customwas chromatographed on silica
  8. washeluting with hexane
  9. customto give the product

Quellen und Nachweise

ORD-Eintrag
ord-9c02a613a35a4deaa8de7d6ce48d66c8
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05206235

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