Hydrochloric Acid → 4,7-Dibromo-1H-indole

HRID 2361430ノート

反応式

HRID 2361430 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[N+:9]([O-])=O.C(=O)=O.[C:15](#N)[CH3:16].C([Mg]Br)=C.[NH4+].[Cl-].Cl>C1COCC1.CCOC(C)=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]2[C:4]=1[CH:15]=[CH:16][NH:9]2

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 770041,4-Dibromo-2-nitrobenzeneHCID 86587134Acetonitrile dry iceHCID 178418507HCID 178418507、化合物

生成物 1

HCID 187528584,7-Dibromo-1H-indole収率 47%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-40 °C

実験手順

To a solution of 1,4-dibromo-2-nitrobenzene (18 g, 64.1 mmol) in THF (200 mL) at −40° C. (dry ice-acetonitrile) was added slowly a solution of vinylmagnesium bromide (1.0 M in THF, 199 mL, 199 mmol). The resulting mixture was stirred at −40° C. for 1.5 h, then was then treated with saturated aqueous NH4Cl (500 mL) and stirred at room temperature for 1 h. HCl (1M) was added to adjust the pH to 7. EtOAc was added and the organic phase was separated, washed with brine, dried and concentrated. The residue was subjected to column chromatography on silica gel (330 g), eluting with EtOAc-hexane (5:95) to provide a light yellow oil which solidified on standing under vacuum. The desired product was obtained as a solid (8.35 g, 47% yield. LCMS showed one major peak with no ionization.

後処理

  1. stirringstirred at room temperature for 1 h
  2. customthe organic phase was separated
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. washeluting with EtOAc-hexane (5:95)
  7. customto provide a light yellow oil which

出典と根拠

ORDレコード
ord-a5aee006fb77407c84420261c894f2bb
出典データセット
uspto-grants-2014_04
特許番号
US08685969B2

反応ノート

読み込み中…