Toluene → 6-Chloro-3'-nitro-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamide

HRID 1894886

Reaktionsgleichung

Reaktionsgleichung von HRID 1894886
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)O1.[Cl:19][C:20]1[CH:38]=[CH:37][C:23]([C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)=[O:25])=[CH:22][C:21]=1I.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>O.C(O)C>[Cl:19][C:20]1[C:21]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)=[CH:22][C:23]([C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:34])([F:35])[F:36])[CH:28]=2)=[O:25])=[CH:37][CH:38]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 112651643-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzeneHCID 690440504-chloro-3-iodo-N-[3-(trifluoromethyl)phenyl]benzamide

Produkt 1

HCID 692724446-Chloro-3'-nitro-N-[3-(trifluoromethyl)phenyl]biphenyl-3-carboxamideAusbeute 146,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

4,4,5,5-Tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane (0.40 g, 0.0016 mol) was mixed with 4-chloro-3-iodo-N-[3-(trifluoromethyl)phenyl]benzamide (0.600 g, 0.00141 mol), potassium carbonate (0.39 g, 0.0028 mol), toluene (10 mL), ethanol (1.7 mL), and water (1.1 mL). The mixture was degassed by bubbling nitrogen through it. To the reaction was added tetrakis(triphenyl-phosphine)palladium(0) (0.078 g, 0.000068 mol). The reaction was heated to reflux for 16 hours. LCMS showed about 80% conversion to M+H 421/423 (3:1). The reaction was extracted with ethyl acetate and the organic extracts were washed with water, saturated NaCl, then dried (Na2SO4). Solvent was removed under vacuum to give 0.87 g oil. The product was purified by automatic flash chromatography on silica gel. Used a 40 g column; flow 40 mL/min; [A=hexane] [B=EtOAc]. A, 4 min; Gradient to 20% B in 30 min. The product eluted in 23-28 min (starting material at 16-18 min). Removal of solvent under vacuum gave 0.46 g white solid.

Aufarbeitung

  1. customThe mixture was degassed
  2. customby bubbling nitrogen through it
  3. temperatureThe reaction was heated
  4. temperatureto reflux for 16 hours
  5. extractionThe reaction was extracted with ethyl acetate
  6. washthe organic extracts were washed with water, saturated NaCl
  7. dry with materialdried (Na2SO4)
  8. customSolvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1f9ca49d310a4510926f8068215a83fc
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513270B2

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