Indole → 1-(4-Fluorobenzyl)-1H-indole

HRID 1977248Notes

Reaction equation

HRID 1977248 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1.O>CS(C)=O>[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 798IndoleHCID 962WaterHCID 96024-Fluorobenzyl chlorideHCID 24758Sodium hydride

Product 1

HCID 9671271-(4-Fluorobenzyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 11.72 g (0.1 mol) of indol in 50 ml of dimethyl sulfoxide is added to a mixture of 2.64 g of sodium hydride (0.11 mol, mineral oil suspension) in 100 ml of dimethyl sulfoxide. The mixture is heated at 60° C. for 1.5 hours, then allowed to cool and 15.9 g (0.11 mol) of 4-fluorobenzyl chloride are added dropwise. The solution is warmed to 60° C., allowed to stand overnight and then poured into 400 ml of water with stirring. The mixture is extracted a number of times with a total of 150 ml of methylene chloride, the organic phase is dried using anhydrous sodium sulfate, filtered and the filtrate is concentrated in vacuo. The residue is distilled in a high vacuum: 21.0 g (96% of theory) b.p. (0.5 mm): 140° C.

Workup

  1. temperatureto cool
  2. temperatureThe solution is warmed to 60° C.
  3. extractionThe mixture is extracted a number of times with a total of 150 ml of methylene chloride
  4. customthe organic phase is dried
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated in vacuo
  7. distillationThe residue is distilled in a high vacuum
  8. custom140° C.

Sources & evidence

ORD record
ord-7a96ecb23e29476caad7a8543c4d9691
Source dataset
uspto-grants-2001_05
Patent number
US06232327B1

Reaction notes

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