Methyl iodide → 1-Bromo-5-chloro-2-methoxy-3-nitrobenzene

HRID 1166225Notes

Reaction equation

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

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 11430Potassium Carbonate

HCID 2918712-Bromo-4-chloro-6-nitrophenol

Product 1

HCID 229976331-Bromo-5-chloro-2-methoxy-3-nitrobenzeneYield 96.5%

Procedure

2-Nitro-4-chloro-6-bromoanisole was prepared by the same procedure as described for Step 2 of Preparation 2a using 2-nitro-4-chloro-6-bromophenol (16 g), methyl iodide (10.8 g), and potassium carbonate (26.3 g). Workup gave crude 2-nitro-4-chloro-6-bromoanisole (16.3 g, 96%) which was used in the next step without purification. 1H NMR (300 MHz, CDCl3) δ7.80 (d, J=2.5 Hz, 1 H), 7.77 (d, J=2.5 Hz, 1H), 4.01 (s, 3H). 13C NMR (75 MHz, CDCl3) δ149.7, 137.2 (2C), 130.0, 124.4, 120.5, 62.8.

Workup

custom2-Nitro-4-chloro-6-bromoanisole was prepared by the same procedure

Sources & evidence

ORD record: ord-7a68c9d600884d29b1dd206b5f0053ac
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613786B2

Reaction notes

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