Propargyl alcohol → 3-(3-Amino-4-Nitrophenyl)-2-propyn-1-ol

HRID 252813Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 252813
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[CH2:12]([OH:15])[C:13]#[CH:14]>COCCOC.C(N(CC)CC)C.ClCCl.[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.[Cu]I>[NH2:8][C:6]1[CH:7]=[C:2]([C:14]#[C:13][CH2:12][OH:15])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Komponenten

8

Edukt 2

HCID 7859Propargyl alcoholHCID 53147665-Bromo-2-nitroaniline

Produkt 1

HCID 597369853-(3-Amino-4-Nitrophenyl)-2-propyn-1-olAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A suspension of bromoarene 2 (447 mg g; 2.06 mmol); tetrakis(triphenylphosphine) palladium(0) (145 mg, 0.12 mmol) and copper(I)iodide (143 mg, 0.75 mmol) in degassed ethyleneglycol dimethylether (2.5 mL) and triethylamine (1.5 mL), was stirred at room temperature under nitrogen in the dark for 10 min and then treated with neat prop-2-yn-1-ol (0.7 mL, 12 mmol) (or any other alkyne of choice, 5 eq.), and the mixture stirred under the same conditions for 48 h, diluted with dichloromethane (50 mL), filtered through a celite pad and concentrated. Purification by flash chromatography (eluent 50 to 75% AcOEt in hexane) afforded compound 72 (328 mg, 83% yield).

Aufarbeitung

  1. filtrationfiltered through a celite pad
  2. concentrationconcentrated
  3. customPurification by flash chromatography (eluent 50 to 75% AcOEt in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-00ed007235bd4f8d9c3b37583f62e169
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868205B2

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