Iodine → 1-Iodo-2-methoxy-4-propoxybenzene

HRID 330834Notes

Reaction equation

HRID 330834 reaction equation
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH3:16])=[CH:9][C:8]=1[O:17][CH3:18].[I:19]I>C1COCC1>[I:19][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH3:16])=[CH:9][C:8]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 807IodineHCID 195949351-Bromo-2-methoxy-4-propoxybenzeneHCID 178418339Butyllithium

Product 1

HCID 666140011-Iodo-2-methoxy-4-propoxybenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

11.1 mL (17.8 mmol) BuLi (1.6M solution in hexane) are added to 3.64 g (14.9 mmol) 1-bromo-2-methoxy-4-propoxybenzene (XXVI.1) in 100 mL THF at −78° C. The mixture is stirred for 5 min at −78° C. After that time, 5.65 g (22.3 mmol) I2 in 10 mL THF are added. The mixture is allowed to reach rt. The solvent is removed in vacuo and the residue is purified by column chromatography (silica gel, heptane/EtOAc 1/1).

Workup

  1. customto reach rt
  2. customThe solvent is removed in vacuo
  3. customthe residue is purified by column chromatography (silica gel, heptane/EtOAc 1/1)

Sources & evidence

ORD record
ord-53475d4e1f03457aae2aa0bfd0a19857
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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