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

HRID 1691813Notes

Reaction equation

HRID 1691813 reaction equation
[F:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([OH:11])=[C:4]([CH3:12])[CH:3]=1.[C:13](=O)([O-])[O-].[Na+].[Na+].IC>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([O:11][CH3:13])=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 108210594-Fluoro-2-methyl-5-nitrophenol

Product 1

HCID 598501391-Fluoro-4-methoxy-5-methyl-2-nitrobenzeneYield 101.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Fluoro-2-methyl-5-nitro-phenol (1.08 g, 6.3 mmol) was dissolved in acetone (100 ml). To this was added solid sodium carbonate (2 eq, 1.34 g) and iodomethane (10 eq, 3.75 ml). The mixture was allowed to stir at room temperature overnight. The mixture was filtered and the filtrate was concentrated in vacuo to give 1-fluoro-4-methoxy-5-methyl-2-nitro-benzene (1.18 g, quantitative) as a pale yellow solid.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e9782aa8ac7f4e1f877dfedc4062d530
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

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