1-Bromo-3-chloropropane → 5-Chloro-1-(3-chloropropyl)indole-3-carboxaldehyde

HRID 2303948Notes

Reaction equation

HRID 2303948 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:13]=[O:14].Br[CH2:16][CH2:17][CH2:18][Cl:19]>CS(C)=O>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:16][CH2:17][CH2:18][Cl:19])[CH:8]=[C:7]2[CH:13]=[O:14]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14797Potassium HydroxideHCID 27953745-chloro-1H-indole-3-carbaldehyde

Product 1

HCID 184620915-Chloro-1-(3-chloropropyl)indole-3-carboxaldehydeYield 84.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred mixture of powdered potassium hydroxide (85%, 2.6 g, 39 mmol) in methyl sulfoxide (20 mL) was added dropwise a solution of 5-chloroindole-3-carboxaldehyde (3.5 g, 19 mmol) in methyl sulfoxide (5 mL). The mixture was stirred for 30 min and 1-bromo-3-chloropropane (2.9 mL, 29 mmol) was added dropwise. The mixture was stirred for 1 h and partitioned between ethyl acetate (3×40 mL) and water (100 mL). The combined organic extracts were washed (water, brine), dried (sodiurn sulfate) and concentrated in vacuo. The solid residue was recrystallised (2-propanol) to give the product as a white solid (4.1 g, 82%): mp 107-108° C.; Found: C, 56.51; H, 4.26; N, 5.44%. C12H11Cl2NO requires: C, 56.27; H, 4.33; N, 5.47%.

Workup

  1. stirringThe mixture was stirred for 1 h
  2. custompartitioned between ethyl acetate (3×40 mL) and water (100 mL)
  3. washThe combined organic extracts were washed (water, brine)
  4. dry with materialdried (sodiurn sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe solid residue was recrystallised (2-propanol)

Sources & evidence

ORD record
ord-3e736621460c4d749d85aa6c010a1c24
Source dataset
uspto-grants-2002_08
Patent number
US06433175B1

Reaction notes

Loading…