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Bicarbonate Ion → Tert-butyl 2-(benzamido)-4-(2-chloro-6-fluorophenyl)benzoate

HRID 1673472
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1673472
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1B(O)O.C(=O)([O-])O.[Na+].[C:17]([NH:25][C:26]1[CH:38]=[C:37](Br)[CH:36]=[CH:35][C:27]=1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Na].C(=O)([O-])O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.C(O)C>[C:17]([NH:25][C:26]1[CH:38]=[C:37]([C:3]2[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH:36]=[CH:35][C:27]=1[C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 769Bicarbonate IonHCID 516892Sodium BicarbonateHCID 35493952-Chloro-6-fluorophenylboronic acid2×HCID 5360545SodiumHCID 67343005Tert-butyl 2-(benzamido)-4-bromobenzoate

Produkt 1

HCID 67342982Tert-butyl 2-(benzamido)-4-(2-chloro-6-fluorophenyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysator2×HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

83 mg of 2-chloro-6-fluorophenylboronic acid, 0.10 g of sodium hydrogen carbonate, 0.6 mL of ethanol, 0.3 mL of wafer and 23 mg of tetrakis(triphenylphosphine)palladium(0) were added to 2.1 mL of toluene solution containing 0.15 g of tert-butyl 2-(benzamido)-4-bromobenzoate, and the resulting mixture was heated to reflux for 2 hours. After the reaction mixture was cooled to room temperature, 21 mg of 2-chloro-6-fluorophenylboronic acid and 23 mg tetrakis(triphenylphosphine)palladium(0) were added and the resulting mixture was heated to reflux for 2 hours. After the reaction mixture was cooled to room temperature, toluene and a saturated sodium, hydrogen carbonate aqueous solution were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane:ethyl acetate=10:1] to obtain tert-butyl 2-(benzamido)-4-(2-chloro-6-fluorophenyl)benzoate.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperaturethe resulting mixture was heated
  4. temperatureto reflux for 2 hours
  5. temperatureAfter the reaction mixture was cooled to room temperature
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. washafter washed with saturated sodium chloride aqueous solution
  9. customthe solvent was evaporated under reduced pressure
  10. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane:ethyl acetate=10:1]

Quellen und Nachweise

ORD-Eintrag
ord-efcd428f124b4f01bce8e2227266ee36
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07999132B2

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