Iodine → 1-Iodo-2-methoxy-4-propoxybenzene
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
Product 1
Reagents, catalysts & solvents 1
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
- customto reach rt
- customThe solvent is removed in vacuo
- 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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