Phosphorus tribromide → 6-Cyano-1-ethyl-2-bromomethyl indole

HRID 1532340ノート

反応式

HRID 1532340 の反応式
P(Br)(Br)[Br:2].[CH2:5]([N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[N:17])[CH:14]=2)[CH:9]=[C:8]1[CH2:18]O)[CH3:6]>ClCCl>[C:16]([C:13]1[CH:14]=[C:15]2[C:10]([CH:9]=[C:8]([CH2:18][Br:2])[N:7]2[CH2:5][CH3:6])=[CH:11][CH:12]=1)#[N:17]

参加物

4

反応物 2

HCID 24614Phosphorus tribromideHCID 212515571-Ethyl-2-(hydroxymethyl)indole-6-carbonitrile

生成物 1

HCID 212515846-Cyano-1-ethyl-2-bromomethyl indole

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

In a 500 ml flask, 18.2 g of 1-ethyl-2-(hydroxymethyl)indole-6-carbonitrile was dissolved in 200 ml of dichloromethane and then cooled to 0° C. 3.45 ml of PBr3 was slowly added thereto, and the mixture was stirred for 4 hours at room temperature. dichloromethane was then added and the reaction mixture was washed with aqueous Na2CO3 solution, diluted with water and then extracted three times with dichloromethane. The organic extracts were combined, dried over MgSO4 and then evaporated to obtain 6-cyano-1-ethyl-2-bromomethyl indole. The resulting product was dissolved in 200 ml of toluene and 30.9 g of triphenylphosphine was added thereto. The mixture was stirred for 10 hours at refluxing temperature and then cooled to room temperature. To this reaction solution was added diethyl ether, and the resulting precipitate was then filtered, washed several times with diethyl ether and dried to obtain 29 g of the title compound as a pale brown solid.

後処理

  1. washthe reaction mixture was washed with aqueous Na2CO3 solution
  2. additiondiluted with water
  3. extractionextracted three times with dichloromethane
  4. dry with materialdried over MgSO4
  5. customevaporated

出典と根拠

ORDレコード
ord-a2d898d53f1a42a292dcff92c55fe9ff
出典データセット
uspto-grants-2001_03
特許番号
US06201006B1

反応ノート

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