Dibromomethane → 1-(Cyclopropylmethyl)-4-methoxybenzene

HRID 645335

Reaktionsgleichung

C(Br)Br.[C:4](Cl)(=O)C.[C:8]1([O:17][CH3:18])[CH:16]=[CH:15][C:11]([CH2:12][CH:13]=[CH2:14])=[CH:10][CH:9]=1.CC(OC)(C)C>C(OCC)C.[Zn].Cl[Cu]>[CH:13]1([CH2:12][C:11]2[CH:15]=[CH:16][C:8]([O:17][CH3:18])=[CH:9][CH:10]=2)[CH2:4][CH2:14]1

Komponenten

Reaktionsbedingungen

Temperatur: 45 °C

Versuchsvorschrift

CH2Br2 (220 g) was added to a slurry of zinc powder (340 g) and CuCl (54 g) in diethyl ether (450 ml). The reaction was started by the addition of acetyl chloride (8 g). The reaction mixture was heated to 45° C. and a solution of estragol (192 g) in ether (150 ml) was added during 25 minutes. Additional CH2Br2 (456 g) dissolved in ether (150 ml) was dropped into the grey-red suspension during 45 minutes. Afterwards, the mixture was stirred at 50° C. for 12 hours. The suspension was cooled to room temperature and MTBE (900 ml) was added. The mixture was filtered through celite, and the filtrate was washed with saturated NH4Cl, water, saturated NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo. The residue was distilled (b.p. 90-95° C./0.1 Torr) to yield 97.5 g (46%) of a colorless oil, which was found to have the following characteristics, NMR and MS spectra.

Aufarbeitung

additionwas dropped into the grey-red suspension during 45 minutes
temperatureThe suspension was cooled to room temperature
filtrationThe mixture was filtered through celite
washthe filtrate was washed with saturated NH4Cl, water, saturated NaHCO3 and brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
distillationThe residue was distilled (b.p. 90-95° C./0.1 Torr)

Quellen und Nachweise

ORD-Eintrag: ord-30f4661058b54a008d52b9a20ce7ef92
Quelldatensatz: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07704942B2

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