Iodine → 5-chloro-2-iodo-1-methyl-1H-indole

HRID 1449622Notes

Reaction equation

HRID 1449622 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[CH:5]2.C([Li])CCC.[I:17]I.S([O-])([O-])=O.[Na+].[Na+]>C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([I:17])=[CH:5]2

Participants

6

Reactant 4

HCID 807IodineHCID 24437Sodium SulfiteHCID 108558435-Chloro-1-methylindoleHCID 178418339Butyllithium

Product 1

HCID 153353185-chloro-2-iodo-1-methyl-1H-indoleYield 93.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 5-chloro-1-methylindole (10.0 g, 60.4 mmole) and n-butyl lithium (29 mL of 2.5 M sol'n in hexanes, 72.5 mmole) in diethyl ether is heated at reflux temperature for 3 hours, cooled to 0° C., treated with iodine (18.4 g, 72.5 mmole), stirred at 0° C. for 1 hour, warmed to room temperature, stirred for 1 hour, and treated with aqueous sodium sulfite. After phase separation, the organic phase is dried over MgSO4 and concentrated in vacuo to give the title product as a brown oil which solidified on standing, 16.5 g (93.7% yield). The title product is used as in Example 4.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 3 hours
  3. temperaturewarmed to room temperature
  4. stirringstirred for 1 hour
  5. customAfter phase separation
  6. dry with materialthe organic phase is dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8953114ba109405d877b5b83f406a7df
Source dataset
uspto-grants-1997_02
Patent number
US05599832

Reaction notes

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