1-Chloro-2-nitrobenzene → 7-chloro-2-methyl-1H-indole

HRID 722398ノート

反応式

HRID 722398 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-])=O.[C:11]([Mg]Br)([CH3:13])=[CH2:12].[NH4+].[Cl-]>C1COCC1>[CH3:13][C:11]1[NH:8][C:3]2[C:4]([CH:12]=1)=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1]

参加物

5

反応物 3

HCID 69451-Chloro-2-nitrobenzeneHCID 25517Ammonium ChlorideHCID 178456138HCID 178456138、化合物

生成物 1

HCID 118160627-chloro-2-methyl-1H-indole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-40 °C

実験手順

Under a nitrogen atmosphere 42.1 g of 2-chloronitrobenzene are placed in 850 ml of THF. The mixture is cooled to −40° C. and then 1.6 1 of isopropenylmagnesium bromide at 0.5 M in THF are added dropwise. After 1 hour at −40° C. with stirring the mixture is hydrolyzed with 400 ml of saturated NH4Cl solution. The aqueous phase is extracted twice with ether. The organic phase is dried and then evaporated and the residue is chromatographed on silica, eluting with toluene. This gives 20.3 g of the expected compound.

後処理

  1. extractionThe aqueous phase is extracted twice with ether
  2. customThe organic phase is dried
  3. customevaporated
  4. customthe residue is chromatographed on silica
  5. washeluting with toluene

出典と根拠

ORDレコード
ord-a7ff061a5a104dbba7c8ac314afe138e
出典データセット
uspto-grants-2006_11
特許番号
US07138424B2

反応ノート

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