Bromine → 3-Bromo-1-(4-ethylbenzy)-1H-indole

HRID 554575Notes

Reaction equation

HRID 554575 reaction equation
[CH2:1]([C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:5][CH:4]=1)[CH3:2].[Br:19]Br.S(OS(O)=O)(O)=O.[Na]>CN(C=O)C>[Br:19][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]([CH2:7][C:6]2[CH:17]=[CH:18][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24193824Sodium pyrosulfurous acidHCID 638117451-(4-Ethylbenzyl)-1H-indole

Product 1

HCID 674612513-Bromo-1-(4-ethylbenzy)-1H-indoleYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1-(4-ethylbenzyl)-1H-indole (2.0 g, 8.50 mmol) in DMF (20 mL) was added dropwise to a solution of bromine (0.46 mL, 8.93 mmol) in DMF (20 mL) at room temperature. The reaction mixture was stirred for two hours, and then poured into an ice-cooled sodium pyrosulfurous acid aqueous solution. The resulting mixture was extracted with ethyl acetate, and the organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The residue was recrystallized from ethyl acetate and n-hexane to obtain the title compound (1.68 g, 63%).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution
  3. dry with materiala saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate)
  4. distillationthe solvent was distilled under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-5db91d3df52b463aa28277e5cb93bbdd
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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