Methyl iodide → 1-Fluoro-2-iodo-4-methoxy-5-methylbenzene

HRID 1438166Notes

Reaction equation

HRID 1438166 reaction equation
[F:1][C:2]1[C:7]([I:8])=[CH:6][C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[C:11]([O-])([O-])=O.[K+].[K+].IC.CCOC(C)=O.CCCCCC>CC(C)=O.C(OCC)C>[CH3:11][O:9][C:5]1[CH:6]=[C:7]([I:8])[C:2]([F:1])=[CH:3][C:4]=1[CH3:10]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 598379984-Fluoro-5-iodo-2-methylphenol

Product 1

HCID 210705041-Fluoro-2-iodo-4-methoxy-5-methylbenzeneYield 70.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To 122C (1 g, 4 mmol) in acetone (20 mL) was added K2CO3 (1.64 g) and iodomethane (0.75 mL). The mixture was stirred at rt for 3 h. After TLC (10% EtOAc/Hexane) indicated the reaction was complete, the mixture was diluted with diethyl ether, washed with water and brine. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography to give 122D (0.75 g, 70% yield). 1H NMR (400 MHz, CDCl3) δ ppm 2.16 (s, 3H) 3.78 (s, 3H) 6.85 (d, J=8.79 Hz, 1H) 7.05 (d, J=5.27 Hz, 1H).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-fac16e442e4044d1b186ddf190ca166b
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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