4'-Bromoacetanilide → N-Acetyl-4-aminobiphenyl

HRID 496942

Reaktionsgleichung

Reaktionsgleichung von HRID 496942
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].[K+].Br[C:13]1[CH:22]=[CH:21][C:16]([NH:17][C:18](=[O:20])[CH3:19])=[CH:15][CH:14]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>[C:18]([NH:17][C:16]1[CH:21]=[CH:22][C:13]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:14][CH:15]=1)(=[O:20])[CH3:19]

Komponenten

6

Edukt 3

HCID 76834'-BromoacetanilideHCID 66827Phenylboronic AcidHCID 522689Potassium Fluoride

Produkt 1

HCID 19998N-Acetyl-4-aminobiphenylAusbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 27342152-(Di-tert-butylphosphino)biphenylKatalysator

Versuchsvorschrift

An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol %), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol %), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4′-bromoacetanilide (214 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 182 mg (86%) of the title compound.

Aufarbeitung

  1. customAn oven dried resealable Schlenk tube
  2. customwas evacuated
  3. customThe tube was evacuated
  4. additionwas added through a rubber septum
  5. customThe tube was sealed with a teflon screwcap
  6. customhad been completely consumed
  7. additionThe reaction mixture was then diluted with ether (30 mL)
  8. filtrationfiltered through celite
  9. concentrationconcentrated
  10. customThe crude material was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-8348f432382b4fea94f28602a0cba331
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06946560B2

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