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

HRID 1681939Notes

Reaction equation

HRID 1681939 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6fcbec8b8d38488d872d04d780feed79
Source dataset
uspto-grants-1992_12
Patent number
US05175164

Reaction notes

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