1-Bromo-3-chloropropane → HCID 21884277, compound

HRID 890240Notes

Reaction equation

HRID 890240 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([CH3:11])=[CH:7]2.[OH-].[K+].[Cl:14][CH2:15][CH2:16][CH2:17]Br>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH:15]([Cl:14])[CH2:16][CH3:17])[C:8]([CH3:11])=[CH:7]2

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14797Potassium HydroxideHCID 118160627-chloro-2-methyl-1H-indole

Product 1

HCID 21884277HCID 21884277, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

40 g of 7-chloro-2-methyl-1H-indole are placed in 60 ml of toluene with 2.8 g of KOH under nitrogen. After stirring for 30 minutes at AT, 7.7 g of 3-chloro-1-bromopropane are added and then the mixture is heated to reflux for 3 hours. The medium is extracted with ether. The organic phase is washed with water, with a 10% HCl solution, with water and with a saturated NaCl solution. It is dried and evaporated and 6.19 g of the expected compound are obtained.

Workup

  1. additionare added
  2. temperaturethe mixture is heated
  3. temperatureto reflux for 3 hours
  4. extractionThe medium is extracted with ether
  5. washThe organic phase is washed with water, with a 10% HCl solution, with water and with a saturated NaCl solution
  6. customIt is dried
  7. customevaporated

Sources & evidence

ORD record
ord-3f7165fa02384a1681ffab5e649b82ee
Source dataset
uspto-grants-2006_02
Patent number
US06995184B2

Reaction notes

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