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

반응식

HRID 2209278 반응식
[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

참가 물질

5

반응물 1

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

생성물 1

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

시약·촉매·용매 3

HCID 23925Iron촉매HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-821b6076d9984c3788665e4dbfaf87f7
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376441B2

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