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

HRID 2065730Notes

Reaction equation

HRID 2065730 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-a23b4e29f72a4e979a2da2e8c2ec8901
Source dataset
uspto-grants-2012_10
Patent number
US08288552B2

Reaction notes

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