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

HRID 1681939

반응식

HRID 1681939 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 10425755N-benzoyl-5-(bromomethyl)indole수율 80%

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6fcbec8b8d38488d872d04d780feed79
출처 데이터셋
uspto-grants-1992_12
특허 번호
US05175164

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