Triethylamine → 3-[(4-Fluorophenyl)ethynyl]aniline

HRID 1030865

Reaktionsgleichung

Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH2:16][C:17]1[CH:18]=[C:19]([C:23]#[CH:24])[CH:20]=[CH:21][CH:22]=1>C1(C)C=CC=CC=1.[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>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:24]#[C:23][C:19]2[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=2)[NH2:16])=[CH:3][CH:4]=1

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

A multinecked flask as described in Example 1 was charged with 50.0 g (0.28 mol) of p-bromofluorobenzene, 200 ml of dried, degassed triethylamine, 35.0 g (0.30 mol) of 3-aminophenylacetylene, 0.23 g (0.29 mmol) of bis(triphenyl phosphine) palladium II chloride, 1.03 g (3.92 mmol) of triphenylphosphine, and 0.1 g (0.52 mmol) of cuprous iodide. The reaction mixture was heated at 65° C. for 48 hours at which point gas chromatography showed the reaction to be complete. The mixture was cooled to room temperature and diluted with 200 ml of toluene. The toluene/triethylamine solution was decanted and concentrated on the rotary evaporator to give 75 g (0.27 mol, 96% yield) of the product as a bright yellow solid.

Aufarbeitung

customA multinecked flask as described in Example 1
customof dried
customthe reaction
temperatureThe mixture was cooled to room temperature
customThe toluene/triethylamine solution was decanted
concentrationconcentrated on the rotary evaporator

Quellen und Nachweise

ORD-Eintrag: ord-f533ca28edf546b5a71de855a664c98e
Quelldatensatz: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05107026

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