Methyl iodide → 2-Bromo-6-methoxynaphthalene

HRID 1840326Notes

Reaction equation

HRID 1840326 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([OH:14])[CH:8]=[CH:7]2.I[CH3:16].[OH-].[Na+]>CS(C)=O>[Br:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH3:16])[CH:10]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 271446-Bromo-2-naphthalenol

Product 1

HCID 787862-Bromo-6-methoxynaphthalene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (60%, 4.5 g, 112 mmol) was added in small portions to a mixture of 6-bromo-2-naphthol (25.0 g, 112 mmol), iodomethane (11.8 g, 168 mmol) and dimethylsulfoxide (150 ml). The mixture was stirred at room temperature overnight. Sodium hydroxide (200 ml, 1 M) was added, and the mixture was filtered. Yield 25.1 g, 95%. Mp 76-82° C.

Workup

  1. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-2e49379b15404ac9801784b308922460
Source dataset
uspto-grants-2004_01
Patent number
US06680328B2

Reaction notes

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