Ammonium Chloride → 4-bromo-6,7-difluoro-1H-indole

HRID 928657ノート

反応式

HRID 928657 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([N+:10]([O-])=O)[C:5]([F:9])=[C:6]([F:8])[CH:7]=1.[CH:13]([Mg]Br)=[CH2:14].C1COCC1.[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[C:4]2[C:3]=1[CH:13]=[CH:14][NH:10]2

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 532162185-Bromo-1,2-difluoro-3-nitrobenzeneHCID 178420667HCID 178420667、化合物

生成物 1

HCID 903842704-bromo-6,7-difluoro-1H-indole収率 12%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-40 °C

実験手順

A solution (20 mL) of 5-Bromo-1,2-difluoro-3-nitrobenzene (1.19 g, 5.00 mmol) in THF was cooled to −50° C. To this, a 1 M vinylmagnesium bromide/THF solution (15 mL) was added dropwise. After the mixture was stirred at −40° C. for 4 hours, a saturated aqueous ammonium chloride solution was added thereto, and concentrated under reduced pressure. The reaction solution was diluted with ethyl acetate, and after washed with saturated brine, the resultant was dried over anhydrous magnesium sulfate. The resultant was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane) to thus obtain the title compound.

後処理

  1. concentrationconcentrated under reduced pressure
  2. additionThe reaction solution was diluted with ethyl acetate
  3. washafter washed with saturated brine
  4. dry with materialthe resultant was dried over anhydrous magnesium sulfate
  5. concentrationThe resultant was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (hexane)

出典と根拠

ORDレコード
ord-10a4fb9beb48464aae2122878b586aee
出典データセット
uspto-grants-2016_03
特許番号
US09290487B2

反応ノート

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