N-bromobutanimide → 7-Bromomethyl-4-ethoxycoumarin

HRID 444222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 444222
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([CH3:22])=[CH:19][CH:20]=2)[O:15][C:14](=[O:23])[CH:13]=1)[CH3:10].N(CCCC#N)=NCCCC#N>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:22][C:18]1[CH:17]=[C:16]2[C:21]([C:12]([O:11][CH2:9][CH3:10])=[CH:13][C:14](=[O:23])[O:15]2)=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 67184N-bromobutanimideHCID 6889444-Ethoxy-7-methylcoumarinHCID 14151322Azobisbutyronitrile

Produkt 1

HCID 134084117-Bromomethyl-4-ethoxycoumarinAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

N-Bromosuccinimide (9.59 g; 0.054 mole) was added to stirred solution of 4-ethoxy-7-methylcoumarin (11 g; 0.054 mole) in carbontetrachloride (600 ml) followed by a catalytic quantity of azo bisbutyronitrile. After refluxing the mixture for 1 hr the solvent was removed in vacuo and the residue recrystallized from ethanol to give 11.73 g (77%) of product of m.p. 150°-3° C. Further recrystallization gave material of m.p. 152°-155° C.

Aufarbeitung

  1. temperatureAfter refluxing the mixture for 1 hr the solvent
  2. customwas removed in vacuo
  3. customthe residue recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-400ef893d00e4b6e843e14d73cc06316
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04263299

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