3-Methyl-2-butanone → 5-BROMO-2,3,3-TRIMETHYL-3H-INDOLE

HRID 252791

Reaction equation

HRID 252791 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]N)=[CH:4][CH:3]=1.[CH3:10][CH:11]([CH3:15])[C:12](=O)[CH3:13]>>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:8]=[C:12]([CH3:13])[C:11]2([CH3:15])[CH3:10]

Participants

3

Reactant 2

HCID 112513-Methyl-2-butanoneHCID 121584-Bromophenylhydrazine

Product 1

HCID 112301415-BROMO-2,3,3-TRIMETHYL-3H-INDOLEYield 87.6%

Procedure

To a 500 mL flask were added p-bromophenylhydrazine 1 (50.3 g, 0.27 mol) glacial acetic acid (300 mL) and 3-methylbutanone (40 mL, 0.37 mol). The mixture was heated at reflux for 4 h and then cooled to rt. The volatile components were removed in vacuo and the residue was partitioned between petroleum ether (350 mL) and water (100 mL). The aqueous phase was washed again with petroleum ether (2×100 mL). The combined organic solutions were dried (MgSO4) and filtered and the solvent was evaporated in vacuo to afford 5-bromo-2,3,3-trimethyl-3H-indole 2 (56.3 g, 87%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 h
  3. customThe volatile components were removed in vacuo
  4. customthe residue was partitioned between petroleum ether (350 mL) and water (100 mL)
  5. washThe aqueous phase was washed again with petroleum ether (2×100 mL)
  6. dry with materialThe combined organic solutions were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-fc5b28c4e2764044b972ac3188c7e6a2
Source dataset
uspto-grants-2011_01
Patent number
US07868157B2

Linked notes

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