1-(4-Bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl ester → 6-bromospiro[benzo[b][1,4]oxazine-2,1'-cyclopropan]-3(4H)-one

HRID 2209278

Reaktionsgleichung

Reaktionsgleichung von HRID 2209278
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2([C:10](OCC)=[O:11])[CH2:9][CH2:8]2)=[C:4]([N+:17]([O-])=O)[CH:3]=1>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[Br:1][C:2]1[CH:16]=[CH:15][C:5]2[O:6][C:7]3([C:10](=[O:11])[NH:17][C:4]=2[CH:3]=1)[CH2:9][CH2:8]3

Komponenten

5

Edukt 1

HCID 583407841-(4-Bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl ester

Produkt 1

HCID 215813596-bromospiro[benzo[b][1,4]oxazine-2,1'-cyclopropan]-3(4H)-oneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Iron (1173 mg, 21 mmol) was added to a solution of ethyl 1-(4-bromo-2-nitrophenoxy)cyclopropanecarboxylate 7.20 (693 mg, 2.1 mmol) in acetic acid (10 mL) at room temperature. Mixture was heated at 60° C. for 5 hours. Mixture was cooled to rt, diluted with 100 mL ethyl acetate, and filtered over celite. Filtrate was concentrated under reduced pressure to yield 6-bromospiro[benzo[b][1,4]oxazine-2,1′-cyclopropan]-3(4H)-one 7.21 (523 mg), which was used in the next step without further purification.

Aufarbeitung

  1. temperatureMixture was cooled to rt
  2. filtrationfiltered over celite
  3. concentrationFiltrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-821b6076d9984c3788665e4dbfaf87f7
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376441B2

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