Methyl iodide → 1-Chloro-4-methoxy-2-methyl-5-nitrobenzene

HRID 1166231

Reaction equation

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

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 11430Potassium Carbonate

HCID 235324-Chloro-5-methyl-2-nitrophenol

Product 1

HCID 158645661-Chloro-4-methoxy-2-methyl-5-nitrobenzeneYield 97.3%

Procedure

4-Chloro-5-methyl-2-nitroanisole was prepared by the same procedure as described for Step 2 of Preparation 2a except using 4-chloro-5-methyl-2-nitrophenol (50 g), methyl iodide (75.8 g), and potassium carbonate (44 g). Workup gave crude 4-chloro-5-methyl-2-nitroanisole (52.3 g, 97%) which was used in the next step without purification. 1H NMR (300 MHz, CDCl3) δ7.85 (s, 1 H), 6.95 (s, 1 H), 3.94 (s, 3 H), 2.45 (s, 3 H).

Workup

custom4-Chloro-5-methyl-2-nitroanisole was prepared by the same procedure

Sources & evidence

ORD record: ord-6cdaa4c65f6b40d1b63eb5d209868180
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613786B2

Linked notes

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