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

Reaction equation

[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

Participants

Conditions

Temperature: 60 °C

Procedure

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.

Workup

temperatureMixture was cooled to rt
filtrationfiltered over celite
concentrationFiltrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-821b6076d9984c3788665e4dbfaf87f7
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376441B2

Linked notes

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