Water → 4-Bromo-5,7-dimethyl-1H-indole

HRID 2278397ノート

反応式

HRID 2278397 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([CH3:11])=[CH:4][C:3]=1[CH3:12].[CH:13]([Mg]Br)=[CH2:14].O>C1COCC1>[Br:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([CH3:11])=[C:6]2[C:7]=1[CH:13]=[CH:14][NH:8]2

参加物

5

反応物 3

HCID 962WaterHCID 124743261-Bromo-2,4-dimethyl-5-nitrobenzeneHCID 178418507HCID 178418507、化合物

生成物 1

HCID 533995074-Bromo-5,7-dimethyl-1H-indole収率 31.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-40 °C

実験手順

To a solution of 1-bromo-2,4-dimethyl-5-nitro-benzene (7.5 g, 32.6 mmol) in THF (100 mL) at −78° C. was added vinylmagnesium bromide (110 mL of 1.0 M solution in THF, 1.1 mol) dropwise. The reaction was allowed to warm slowly to −40° C. then stirred for 4 h. Water was added, and the reaction mixture allowed to warm slowly to rt and extracted with EtOAc. The organic phase was then dried over Na2SO4 and concentrated to give 4-bromo-5,7-dimethylindole (2.3 g) which was used in the subsequent step without purification.

後処理

  1. temperatureto warm slowly to rt
  2. extractionextracted with EtOAc
  3. dry with materialThe organic phase was then dried over Na2SO4
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-fe90991f25d94f1b84f42f8b971910a3
出典データセット
uspto-grants-2015_09
特許番号
US09133180B2

反応ノート

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