Water → 2-Iodo-1-(methyloxy)-3-[(2-methyl-2-propen-1-yl)oxy]benzene

HRID 1484625Notes

Reaction equation

HRID 1484625 reaction equation
[I:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:10].[H-].[Na+].Cl[CH2:14][C:15]([CH3:17])=[CH2:16].O>CN(C=O)C>[I:1][C:2]1[C:3]([O:10][CH2:16][C:15]([CH3:17])=[CH2:14])=[CH:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 112413-Chloro-2-methyl-1-propeneHCID 24758Sodium hydrideHCID 141047372-Iodo-3-methoxyphenol2×

Product 1

HCID 679668282-Iodo-1-(methyloxy)-3-[(2-methyl-2-propen-1-yl)oxy]benzeneYield 92.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-iodo-3-(methyloxy)phenol (Intermediate 3, 10.3 g) in DMF (100 ml, SCRC) was added NaH (60%, wt., 1.977 g, 49.4 mmol) portionwise. The reaction mixture was stirred at room temperature for 1 hour and 3-chloro-2-methyl-1-propene (3.73 g, 41.2 mmol, Aldrich) was added. The resulting mixture was stirred at room temperature for 2 hours and water (50 ml) was added. The reaction mixture was extracted with ethyl acetate (3 times 200 ml, SCRC) and the combined organic layer were dried, evaporated and purified by silica gel chromatography with as eluents EtOAc/PE (1/30) to afford the title compound as a yellow liquid (11.6 g)

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 2 hours
  2. extractionThe reaction mixture was extracted with ethyl acetate (3 times 200 ml, SCRC)
  3. customthe combined organic layer were dried
  4. customevaporated
  5. custompurified by silica gel chromatography with as eluents EtOAc/PE (1/30)

Sources & evidence

ORD record
ord-b86690a5bc0044fda6c33d8b15fc0b3e
Source dataset
uspto-grants-2016_08
Patent number
US09422272B2

Reaction notes

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