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

反応式

HRID 2209278 の反応式
[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

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 176Acetic Acid溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-821b6076d9984c3788665e4dbfaf87f7
出典データセット
uspto-grants-2016_06
特許番号
US09376441B2

関連ノート

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