Sodium Chloride → 7-bromo-2-ethyl-1H-indole

HRID 890235ノート

反応式

HRID 890235 の反応式
[Mg].Br[C:3]([CH2:5][CH3:6])=[CH2:4].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-])=O.[Na+].[Cl-]>C1COCC1>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:9]=1[NH:14][C:3]([CH2:5][CH3:6])=[CH:4]2

参加物

6

反応物 4

HCID 5234Sodium ChlorideHCID 113411-Bromo-2-nitrobenzeneHCID 899901-Butene, 2-bromo-2 回HCID 5462224Magnesium2 回

生成物 1

HCID 222505807-bromo-2-ethyl-1H-indole収率 207.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒4 回

反応条件

温度
60 °C

実験手順

2.4 g of magnesium are placed in a round-bottomed flask and the magnesium is covered with 10 ml of THF. 1 g of 2-bromo-1-butene, then 10 ml of THF and then again 12.5 g of 2-bromo-1-butene in 30 ml of THF are added. The reaction medium is observed to warm up and then it is heated at 60° C. for 30 minutes after the end of the addition reaction. The mixture is subsequently cooled to −20° C., 20 ml of THF are added and then 6.7 g of 2-bromonitrobenzene are added at −20° C. The mixture is allowed to return to AT. The reaction medium is poured onto 200 ml of a saturated NaCl solution. Extraction is carried out with ether, the extracts are then evaporated and the residue is taken up in DCM. The organic phase is washed with water and then with a saturated NaCl solution. It is dried and evaporated and then the residue is chromatographed on silica while eluting with a cyclohexane/AcOEt (9.5/0.5, v/v) mixture. 3.45 g of the expected compound are obtained.

後処理

  1. temperatureto warm up
  2. additionafter the end of the addition reaction
  3. temperatureThe mixture is subsequently cooled to −20° C.
  4. extractionExtraction
  5. customthe extracts are then evaporated
  6. washThe organic phase is washed with water
  7. customIt is dried
  8. customevaporated
  9. customthe residue is chromatographed on silica
  10. washwhile eluting with a cyclohexane/AcOEt (9.5/0.5

出典と根拠

ORDレコード
ord-a97595312546450ca0c9737b930206f5
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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