Bromotrichloromethane → Methyl 3-(dichloromethylene)-2,3-dihydro-1-benzoxepin-7-carboxylate

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Reaktionsgleichung

Br[C:2]([Cl:5])(Cl)[Cl:3].O=[C:7]1[CH:13]=[CH:12][C:11]2[CH:14]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH:16]=[CH:17][C:10]=2[O:9][CH2:8]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[Cl:3][C:2]([Cl:5])=[C:7]1[CH:13]=[CH:12][C:11]2[CH:14]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH:16]=[CH:17][C:10]=2[O:9][CH2:8]1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

0.046 ml (2 equivalents) of bromotrichloromethane is added to 50 mg (0.23 mmol) of methyl 3-oxo-2,3-dihydro-1-benzoxepin-7-carboxylate, prepared according to example 49, and 214 mg (0.92 mmol) of triphenylphosphine in suspension in 0.5 ml of acetonitrile, which is stirred beforehand at 0° C. for 2 hours. The reaction medium is protected from light and is again stirred at ambient temperature for 15 minutes. After the conventional treatments, purification on a column of silica gel (ethyl acetate/heptane 5/95) provides 48 mg (74%) of methyl 3-(dichloromethylene)-2,3-dihydro-1-benzoxepin-7-carboxylate in the form of a white solid; M.p.=119–121° C.

Aufarbeitung

customprepared
stirringis again stirred at ambient temperature for 15 minutes
customAfter the conventional treatments, purification on a column of silica gel (ethyl acetate/heptane 5/95)

Quellen und Nachweise

ORD-Eintrag: ord-4bb72300ba5c4c05b76cf13a23b63ef4
Quelldatensatz: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07071340B2

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