Bromide ion → 3-Bromo-1h-indole

HRID 1182325Notes

Reaction equation

HRID 1182325 reaction equation
[Br-:1].COC1C=CC(C(O)C2C=CC(OC)=CC=2)=CC=1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23](S(O)(=O)=O)=[CH:22][CH:21]=1.C[N:32]1[CH2:36]CCC1=O>C1C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:30]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:32][CH:36]=1

Participants

7

Reactant 4

HCID 259Bromide ionHCID 6101p-Toluenesulfonic acidHCID 13387N-methyl-2-pyrrolidoneHCID 69768p,p'-Dimethoxybenzhydryl alcohol

Product 1

HCID 27632773-Bromo-1h-indoleYield 87%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the above bromide (1.09 g, 2.8 mmol) was added 4,4′-dimethoxybenzhydrol (818 mg, 3.4 mmol) and p-toluenesulfonic acid (532 mg, 2.8 mmol) in benzene (60 mL) and N-methylpyrrolidinone (6 mL) were heated to reflux. After 24 h the reaction was allowed to cool to room temperature and diluted with ethyl acetate (200 mL). The organic layer was washed with NaHCO3 (2×), H2O (2×), and Brine(2×), dried over anhydrous MgSO4, filtered and the solvent removed in vacuo. The crude material was purified via column chromatography (10% EtOAc-Hexane) to provide the desired DMB protected 3-bromoindole derivative (1.5 g, 2.4 mmol, 87% yield) as an orange solid: (ESII-MS (M+H) 616.5 m/e).

Workup

  1. temperaturewere heated to reflux
  2. washThe organic layer was washed with NaHCO3 (2×), H2O (2×), and Brine(2×)
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe crude material was purified via column chromatography (10% EtOAc-Hexane)
  7. customto provide the desired DMB

Sources & evidence

ORD record
ord-36550624e3fe4511bc18e379e90afd1c
Source dataset
uspto-grants-2007_10
Patent number
US07288650B2

Reaction notes

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