1-Fluoro-3-iodobenzene → Tert-butyl 3-(3-fluorophenyl)prop-2-ynoate

HRID 523116

Reaktionsgleichung

[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[C:2]#[CH:3].[Mg+2].[Cl-].[Cl-].[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16](I)[CH:15]=1>C1COCC1.[NH4+].[Cl-].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>[F:13][C:14]1[CH:15]=[C:16]([C:3]#[C:2][C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH:17]=[CH:18][CH:19]=1

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

A dry, argon-filled Schlenk tube with a magnetic stirrer bar and septum is initially charged with tert-butyl prop-2-ynoate (70 mg, 0.56 mmol) in anhydrous THF (2 ml). After adding (TMP)2Zn.MgCl2 (2.2 ml, 1.2 mmol) at 25° C., the mixture is stirred for 30 min, then a solution of 1-fluoro-3-iodobenzene (160 mg, 0.72 mmol), tetrakis(triphenylphosphine)palladium(0) (33 mg, 5 mol %) in anhydrous THF (2 ml) is added dropwise and the mixture is stirred at 25° C. overnight. For workup, the mixture is diluted with aqueous sat. NH4Cl solution (30 ml) and extracted with ethyl acetate (3×30 ml). After the combined organic phases have been dried over Na2SO4, the solvent has been distilled off and purification has been effected by column chromatography on silica gel (heptane:ethyl acetate), the desired compound (91 mg, 75% of theory) was obtained as a colourless oil.

Aufarbeitung

additionA dry, argon-filled Schlenk tube with a magnetic stirrer bar
additionAfter adding (TMP)2Zn
extractionextracted with ethyl acetate (3×30 ml)
dry with materialAfter the combined organic phases have been dried over Na2SO4
distillationthe solvent has been distilled off
custompurification

Quellen und Nachweise

ORD-Eintrag: ord-2ce4876180e64b929f40fda87d2399cc
Quelldatensatz: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09334292B2

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