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

HRID 890234ノート

反応式

HRID 890234 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

42.1 g of 2-chloronitrobenzene are placed in 850 ml of THF under a nitrogen atmosphere. The mixture is cooled to −40° C. and then 1.61 of 0.5M isopropenylmagnesium bromide in THF are added dropwise. After stirring at −40° C. for 1 hour, the mixture is hydrolysed with 400 ml of a 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 while eluting with toluene. 20.3 g of the expected compound are obtained.

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. washwhile eluting with toluene

出典と根拠

ORDレコード
ord-e351a1fcc9084239a1e475239f2a9247
出典データセット
uspto-grants-2006_02
特許番号
US06995184B2

反応ノート

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