Ethyl 3-(4-bromophenyl)-2-cyanoacrylate → Ethyl 3-(4-bromophenyl)-2-cyano-3-o-tolylpropanoate

HRID 1527961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527961
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](\[C:15]#[N:16])/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[C:17]1([CH3:25])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[Mg]Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH3:25])[CH:9]([C:15]#[N:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 5378084Ethyl 3-(4-bromophenyl)-2-cyanoacrylateHCID 178424304HCID 178424304, Verbindung

Produkt 1

HCID 67015643Ethyl 3-(4-bromophenyl)-2-cyano-3-o-tolylpropanoateAusbeute 107,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A solution of (E)-ethyl 3-(4-bromophenyl)-2-cyanoacrylate (59.4 g, 212 mmol) in toluene (420 mL) was added over 80 min at 0-5° C. to o-tolylmagnesium chloride solution (1 M in tetrahydrofuran, 276 mL, 276 mmol). The reaction mixture was heated at 85° C. for 1½ h, then poured upon ice water and partitioned between 1 M aq. hydrochloric acid solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated to produce the title compound (84.6 g), which was directly used in the next step. Light yellow oil, MS: 370.0 [M−H]−.

Aufarbeitung

  1. custompartitioned between 1 M aq. hydrochloric acid solution and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ca07a5e479184607bd9a07b9fb093f19
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090565B2

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