N-bromobutanimide → N-benzoyl-5-(bromomethyl)indole

HRID 1681939

反応式

HRID 1681939 の反応式
[C:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=2)[CH:11]=[CH:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[C:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][Br:19])=[CH:15][CH:16]=2)[CH:11]=[CH:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 10354051N-benzoyl-5-methylindole

生成物 1

HCID 10425755N-benzoyl-5-(bromomethyl)indole収率 80%

試薬・触媒・溶媒 2

HCID 5943Carbon Tetrachloride溶媒HCID 6344Dichloromethane溶媒

実験手順

A suspension of the product of Step A (5.5 g 23.4 mmol) in 10 mL of CCl4 was heated to reflux. N-bromosuccinimide (4.6 g, 25.7 mmol) and several crystals (approximately 100 mg) of azoisobutyronitrile (AIBN) were added. The resultant solution was stirred at reflux for 4 hours. The solution was cooled, diluted with 1.5 L of CH2Cl2 and washed with 400 mL of H2O and 400 mL of brine. The organic phase was dried over MgSO4, filtered and concentrated to a brown oil. The resultant oil was flash chromatographed eluting with 10:1 hexane/ethyl acetate to afford the titled compound (5.6g, 80%) as a yellow powder.

後処理

  1. temperaturewas heated to reflux
  2. temperatureat reflux for 4 hours
  3. temperatureThe solution was cooled
  4. washwashed with 400 mL of H2O and 400 mL of brine
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to a brown oil
  8. customchromatographed
  9. washeluting with 10:1 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-6fcbec8b8d38488d872d04d780feed79
出典データセット
uspto-grants-1992_12
特許番号
US05175164

関連ノート

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