Methyl iodide → 2,6-Dichloro-4-nitroanisole

HRID 1166229Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[OH:12].CI.[C:15](=O)([O-])[O-].[K+].[K+]>>[N+:9]([C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[O:12][CH3:15])([O-:11])=[O:10]

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 11430Potassium Carbonate

HCID 118712,4-Dichloro-6-nitrophenol

Product 1

HCID 1698622,6-Dichloro-4-nitroanisoleYield 90.1%

Procedure

2-Nitro-4,6-dichloroanisole was prepared by the same procedure as described for Step 2 of Preparation 2a except using 2,4-dichloro-6-nitrophenol (52 g), methyl iodide (71 g), and potassium carbonate (41.4 g). Workup gave crude 2-nitro-4,6-dichloroanisole (50 g, 90%) which was used in the next step without purification.

Workup

custom2-Nitro-4,6-dichloroanisole was prepared by the same procedure

Sources & evidence

ORD record: ord-d012ac83f92c48888a9beb0d02d2ccbf
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613786B2

Reaction notes

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