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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 4-bromo-7-(ethoxycarbonyl)-3-fluoro-9H-carbazole-1-carboxylic acid

HRID 523239
ノート
印刷プレビュー

反応式

HRID 523239 の反応式
[Br:1][C:2]1[C:14]([F:15])=[CH:13][C:12]([C:16]([OH:18])=[O:17])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:8][C:9]=1[NH:10]2.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[C:3]2[C:4]3[C:9](=[CH:8][C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6][CH:5]=3)[NH:10][C:11]=2[C:12]([C:16]([OH:18])=[O:17])=[CH:13][C:14]=1[F:15]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 1177608064-bromo-7-ethoxycarbonyl-3-fluoro-6,7,8,9-tetrahydro-5H-carbazole-1-carboxylic acid

生成物 1

HCID 1177608524-bromo-7-(ethoxycarbonyl)-3-fluoro-9H-carbazole-1-carboxylic acid収率 84.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate
溶媒

実験手順

A solution of 5-bromo-2-(ethoxycarbonyl)-6-fluoro-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid (2.87 g, 7.47 mmol) and 2,3-dichloro-5,6-dicyanobenzoquinone (3.73 g, 16.4 mmol) in THF (45 mL) was heated at 60° C. for 90 min. The cooled mixture was diluted with EtOAc (about 50 mL) and stirred for 60 min. The resulting precipitate was collected by filtration, washed with EtOAc and dried. The filtrate was concentrated, and the residue was triturated with MeOH with sonication, filtered, and the precipitate was washed with MeOH and dried. The two precipitates were combined to give 4-bromo-7-ethoxycarbonyl-3-fluoro-9H-carbazole-1-carboxylic acid as a pale yellow solid (2.39 g, 84% yield). Mass spectrum m/z 380, 382 (M+H)+.

後処理

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with EtOAc
  3. customdried
  4. concentrationThe filtrate was concentrated
  5. customthe residue was triturated with MeOH with sonication
  6. filtrationfiltered
  7. washthe precipitate was washed with MeOH
  8. customdried
  9. customThe two precipitates

出典と根拠

ORDレコード
ord-43bec32b56b2485487a801832950296c
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09334290B2

反応ノート

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