2,4-Dichlorobenzyl chloride → HCID 21938270, compound

HRID 1242136Notes

Reaction equation

HRID 1242136 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[C:10]([CH3:14])[NH:11]2)=[CH:7][CH:6]=1)=[O:4].[Cl:15][C:16]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:17]=1[CH2:18]Cl>O1CCOCC1.[Ag-]=O>[Cl:15][C:16]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:17]=1[CH2:18][C:9]1[C:8]2[C:12](=[CH:13][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)[NH:11][C:10]=1[CH3:14]

Participants

5

Reactant 2

HCID 72122,4-Dichlorobenzyl chlorideHCID 11435419HCID 11435419, compound

Product 1

HCID 21938270HCID 21938270, compoundYield 20.6%

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

6-(Methoxycarbonyl)-2-methylindole (3.03 g), 2,4-dichlorobenzyl chloride (4.69 g) and silver(I) oxide (5.56 g) are suspended in 1,4-dioxane (50 ml), and stirred under heat at 90° C. for 19.5 hours. The solid is separated through filtration, and the filtrate is concentrated. The resulting residue is purified through silica gel column chromatography to obtain 3-(2,4-dichlorobenzyl)-6-(methoxycarbonyl)-2-methylindole (58) (1.15 g).

Workup

  1. customThe solid is separated through filtration
  2. concentrationthe filtrate is concentrated
  3. customThe resulting residue is purified through silica gel column chromatography

Sources & evidence

ORD record
ord-b0172d35a7c64cc3aba04e8d0a41e815
Source dataset
uspto-grants-2006_10
Patent number
US07115647B2

Reaction notes

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