Phenylboronic Acid → HCID 23033929, Verbindung

HRID 1393352Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1393352
C(=O)(O)[O-].[Na+].Br[C:7]1[S:8][C:9]2[C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O.C(COC)OC.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.[Cu]I>[C:19]1([C:7]2[S:8][C:9]3[C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

8

Edukt 3

HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 230338792-Bromo-1,3-benzothiazole-7-carboxylic acid

Produkt 1

HCID 23033929HCID 23033929, VerbindungAusbeute 78,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium (144 mg, 0.125 mmol) and a solution of sodium bicarbonate (630 mg, 7.50 mmol) in degassed water (10 ml) were added in turn to a solution of ethyl ester of 2-bromobenzothiazole-7-carboxylic acid (715 mg, 2.50 mmol) and phenyl boronic acid (341 mg, 2.8 mmol) in degassed dimethoxyethane (20 ml) and the mixture was stirred at 50° C. for 10 min. Copper (I) iodide (24 mg, 0.125 mmol) was added to the mixture at room temperature and the mixture was heated under reflux for 4 hrs. Dimethoxyethane was distilled off under reduced pressure and the residue was extracted with ethyl acetate. The organic layer was washed with brine and dried and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=10) to give ethyl ester of 2-phenylbenzothiazole-7-carboxylic acid (500 mg, 70%) as colorless crystals.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. distillationDimethoxyethane was distilled off under reduced pressure
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customdried
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=10)

Quellen und Nachweise

ORD-Eintrag
ord-74687d80904c4c35b0ab8edea982053f
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07345068B2

Notizen zur Reaktion

Wird geladen…