Iodine → 6-Chloro-2-iodo-1-methyl-1H-indole

HRID 1449627Notes

Reaction equation

HRID 1449627 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.C([Li])(C)(C)C.[I:17]I.S([O-])([O-])=O.[Na+].[Na+]>C(OCC)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([I:17])[N:8]2[CH3:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 807IodineHCID 24437Sodium SulfiteHCID 153353216-Chloro-1-methyl-1H-indoleHCID 178418306HCID 178418306, compound

Product 1

HCID 153353226-Chloro-2-iodo-1-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 6-chloro-l-methylindole (0.83 g, 5.0 mmole) in diethyl ether is treated with 1.7 M t-butyl lithium in hexanes (3.5 mL, 6.0 mmole) at 0° C., stirred at ambient temperatures for 0.25 hour, treated with I2 (1.52 g, 6.0 mmole), stirred at room temperature until reaction is complete by TLC analysis, treated with aqueous sodium sulfite and extracted with diethyl ether. The combined ether extracts are dried over MgSO4 and concentrated in vacuo to afford the title product as a brown solid, 1.52 g (contains ether). The product is used as is in Example 9.

Workup

  1. stirringstirred at room temperature until reaction
  2. extractionextracted with diethyl ether
  3. dry with materialThe combined ether extracts are dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d055ecb95fb64707afe30f5bce44af9a
Source dataset
uspto-grants-1997_02
Patent number
US05599832

Reaction notes

Loading…