1,3-Dibromopropane → HCID 86699688, compound

HRID 1487216Notes

Reaction equation

HRID 1487216 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)([O-:3])=[O:2].[OH-].[K+].[Br:15][CH2:16][CH2:17][CH2:18]Br>CN(C=O)C.O>[Br:15][CH2:16][CH2:17][CH2:18][N:8]1[C:9]2[C:5](=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7]1

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 14797Potassium HydroxideHCID 1457664-Nitro-1H-indole

Product 1

HCID 86699688HCID 86699688, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-nitroindole (5 g, 31 mmol) in anhydrous N,N′-dimethylformamide (200 mL) was added grounded potassium hydroxide (1.74 g, 31 mmol) in portions. Then a solution of 1,3-dibromopropane (18 g, 89 mmol) in N,N′-dimethylformamide was added dropwise. The mixture was stirred at room temperature for 12 hours, diluted with water and extracted with ethyl acetate. The organic phases were combined, washed by brine, dried over anhydrous sodium sulfate, filtrated and evaporated. The residue was purified by silica gel chromatography to afford the product 1-(3-bromopropyl)-4-nitro-1H-indole as brown-red oil (8.18 g, yield 94%).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed by brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltrated
  5. customevaporated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7b1aa463b3924e8980535cce3d85f5a5
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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