Methyl iodide → 4-methoxy-4'-methylbiphenyl-3-yl-phosphonic Acid Dimethyl Ester

HRID 1018972Notes

Reaction equation

HRID 1018972 reaction equation
[CH3:1][O:2][P:3]([C:7]1[CH:8]=[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:10]=[CH:11][C:12]=1[OH:13])(=[O:6])[O:4][CH3:5].I[CH3:22].[OH-].[Na+]>CN(C=O)C>[CH3:1][O:2][P:3]([C:7]1[CH:8]=[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:22])(=[O:6])[O:4][CH3:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 18342343HCID 18342343, compound

Product 1

HCID 599208424-methoxy-4'-methylbiphenyl-3-yl-phosphonic Acid Dimethyl EsterYield 63.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-hydroxy-4′-methylbiphenyl-3-yl-phosphonic acid dimethyl ester (500 mg, 1.7 mmol), iodomethane (342 mg, 2.4 mmol) and 10 M aqueous NaOH (190 μL, 1.9 mmol) in DMF (10 mL) was stirred at r.t. overnight. After dilution with H2O, the mixture was extracted with EtOAc. Chromatography over silica gel and elution with EtOAc with 5% of MeOH gave 330 mg (63%) of title compound as a white solid.

Workup

  1. extractionAfter dilution with H2O, the mixture was extracted with EtOAc
  2. washChromatography over silica gel and elution with EtOAc with 5% of MeOH

Sources & evidence

ORD record
ord-35eb466e164b479ea2fc4897e87333b5
Source dataset
uspto-grants-2002_11
Patent number
US06486141B2

Reaction notes

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