Methyl iodide → 4-Methoxydibenzofuran

HRID 2383971Notes

Reaction equation

HRID 2383971 reaction equation
[H-].[Na+].[CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[O:8][C:7]=2[C:6]([OH:16])=[CH:5][CH:4]=1.[CH3:17]I>CN(C=O)C>[CH3:17][O:16][C:6]1[C:7]2[O:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[C:11]=2[CH:3]=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 30150514-Dibenzofuranol

Product 1

HCID 119941974-Methoxydibenzofuran

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of 50% NaH (15.6 g, 0.32 mol) in DMF (100 ml), a solution of dibenzofuran-4-ol (40 g, 0.217 mol) in DMF (200 ml) was added drop wise at 0-5° C. under stirring and under a nitrogen atmosphere. The reaction mass was allowed to stir for 15 min at a temperature of 0-5° C. under N2. A solution of methyl iodide (20.3 ml, 0.32 mol) in DMF (50 ml) was added drop wise at 0-5° C. and the reaction mass was allowed to stir for 1 hr at room temperature. When TLC confirmed absence of starting material, the reaction mass was quenched with water and extracted with ethyl acetate. The organic layer was dried with sodium sulfate and evaporated under vacuum to give product 4-Methoxydibenzofuran. Yield 43 g (98%)

Workup

  1. stirringto stir for 15 min at a temperature of 0-5° C. under N2
  2. stirringto stir for 1 hr at room temperature
  3. customthe reaction mass was quenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-2f22714845ef4426bf212c86aa2da568
Source dataset
uspto-grants-2012_09
Patent number
US08263648B2

Reaction notes

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